Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments Synthesis (IF 2.650) Pub Date : 2017-11-16 Sayini, Ramakrishna, Srihari, Pabbaraja
The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.
Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones Synthesis (IF 2.650) Pub Date : 2017-11-14 Ayadi, Marwa, Mpawenayo, Pierre C., Rezgui, Farhat, Leclerc, Eric, Vrancken, Emmanuel, Campagne, Jean-Marc
An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.
Bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane as Unique Metal Ligand: Self-Assembly of Palladium Nanoparticles and Catalytic Reactivity on C–C Bond Formation Synthesis (IF 2.650) Pub Date : 2017-11-13 Fujiki, Katsumasa, Tanaka, Katsunori
A previously unreported 1,5-diazacyclooctane-palladium(II) complex was synthesized using bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane, which was readily prepared via a novel [4+4] homocyclization of the unsaturated imine intermediate generated from acrolein and 1-amino-2-indanol. Interestingly, the 1,5-diazacyclooctane-palladium(II) complex self-assembled to form palladium nanoparticles. This approach readily provided palladium nanoparticles simply by heating a mixture of palladium(II) acetate and bis[N,N′-(2-indanolyl)]-1,4-diazacyclooctane in dichloroethane at mild temperatures. The 1,5-diazacyclooctane-derivative-palladium nanoparticles were successfully deployed in synthetic applications as a heterogeneous catalyst, facilitating Suzuki coupling and a challenging C–C bond formation via C(sp3)–H activation under low catalyst loading conditions.
Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxybenzophenone Synthesis (IF 2.650) Pub Date : 2017-11-09 Gugkaeva, Zalina T., Larionov, Vladimir A., Moskalenko, Margarita A., Khrustalev, Victor N., Nelyubina, Yulia V., Peregudov, Alexander S., Tsaloev, Alan T., Maleev, Victor I., Belokon, Yuri N.
We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).
Asymmetric Chlorination of Cyclic β-Keto Esters and N-Boc Oxindoles Catalyzed by an Iron(III)-BPsalan Complex Synthesis (IF 2.650) Pub Date : 2017-11-09 Luo, Yong-Heng, Ping, Yuan-Ji, Li, Zong-Rui, Gu, Xin, Xu, Zhen-Jiang, Che, Chi-Ming
An iron(III)-BPsalan complex was found to efficiently catalyze the asymmetric chlorination reaction of cyclic β-keto esters and N-Boc oxindoles, affording the corresponding chlorinated products in high yield and up to 92% ee with NCS as chlorination reagent under mild reaction conditions.
Synthesis of 1,5-Anhydro-d-glycero-d-gluco-heptitol Derivatives as Potential Inhibitors of Bacterial Heptose Biosynthetic Pathways Synthesis (IF 2.650) Pub Date : 2017-11-08 Blaukopf, Markus, Atamanyuk, Dmytro, Xavier, Nuno M., Gerusz, Vincent, Kosma, Paul
A series of 1,5-anhydro-d-glycero-d-gluco-heptitol derivatives have been prepared from 3-O-benzyl-1,2-O-isopropylidene-d-glycero-d-gluco-heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d-glycero-d-gluco- and 1,2-dideoxy-d-altro- configuration as well as the 1,5-anhydro-2-deoxy-d-altro-hept-1-enitol. In addition, the 7-O-phosphorylated d-glycero-d-gluco-heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.
Synthesis of Monofunctionalized Calixarenes Synthesis (IF 2.650) Pub Date : 2017-11-08 Ingenfeld, Björn, Straub, Steffen, Frömbgen, Christopher, Lützen, Arne
Seven OH-free and O-permethylated monofunctionalized calixarenes carrying either additional methyl or tert-butyl groups are prepared following fragment condensation protocols. This strategy proves to be superior to previous approaches. Calixarenes with free OH groups all adopt a cone conformation stabilized by a seam of hydrogen bonds at the lower rim. Post-condensation modifications, i.e., methylation of phenolic OH groups or functional group interconversions can also be achieved. Bulky tert-butyl groups are also found to stabilize the cone conformations of O-methylated compounds. These compounds offer versatile functional groups that make these concave molecules interesting building blocks for the synthesis of more sophisticated molecular architectures.
Recent Progress on Radical Decarboxylative Alkylation for Csp3–C Bond Formation Synthesis (IF 2.650) Pub Date : 2017-11-08 Li, Yajun, Ge, Liang, Muhammad, Munira Taj, Bao, Hongli
Radical decarboxylation has emerged as an attractive method for the formation of C–C bonds starting from easily accessible carboxylic acids. In this review, we attempt to bring the readers up to date in this rapidly expanding field. Specifically, we will cover recent advances in Csp3–C bond formation via the radical decarboxylation of aliphatic carboxylic acids and their activated forms, such as N-hydroxyphthalimide esters (NHP esters), alkyl diacyl peroxides, alkyl peresters, and aryliodine(III) dicarboxylates. The scope and limitation of these transformations will be discussed, highlighting gaps in knowledge and research and examining the mechanisms underlying radical decarboxylation. We aim to make this review a stepping stone for further development in this field.
Improved Synthesis of Racemate and Enantiomers of Taniguchi Lactone and Conversion of Their C–C Double Bonds into Triple Bonds Synthesis (IF 2.650) Pub Date : 2017-11-07 Malová Križková, Petra, Lindner, Wolfgang, Hammerschmidt, Friedrich
cis-2-Butene-1,4-diol was heated with triethyl orthoacetate and p-hydroquinone as catalyst at 170 °C to give racemic Taniguchi lactone. It was converted into diastereomeric amides with (S)-1-phenylethylamine for stereoisomer resolution. The double bonds of (±)-, (R)- and (S)-Taniguchi lactones were brominated and dehydrobrominated in two steps, using at first DBU and then LDA, to deliver the triple bonds.
Glycosylation of Stannyl Ceramides Promoted by Modified Montmorillonite in Supercritical Carbon Dioxide Synthesis (IF 2.650) Pub Date : 2017-11-07 Morales-Serna, José Antonio, Nguyen, Bao N., García-Ríos, Eréndira, Gaviño, Rubén, Cárdenas, Jorge, García de la Mora, Gustavo
The direct glycosylation of ceramides in supercritical carbon dioxide (scCO2) successfully proceeded to produce β-glycolipids in high yield and with full stereoselectivity. The reaction is promoted by montmorillonite modified with a superacid (CF3SO3H). The value of this protocol was demonstrated in the efficient synthesis of isoglobotrihexosylceramide (iGB3).
Recent Advances in the Synthesis of β-Ketonitriles Synthesis (IF 2.650) Pub Date : 2017-11-07 Kiyokawa, Kensuke, Nagata, Takaya, Minakata, Satoshi
β-Ketonitriles are an important class of compounds in the field of organic and medicinal chemistry. Over the past decades, numerous efforts have been devoted to the development of new and efficient methodologies for the synthesis of these derivatives, and a number of efficient methods to accomplish this have been developed in recent years. In this context, this short review highlights recent advances in the synthesis of β-ketonitriles.
Friedel–Crafts Alkylation of Aromatics by TiCl4-Promoted Ring Cleavage of 3-Arylcyclobutanones Synthesis (IF 2.650) Pub Date : 2017-11-06 Kanie, Mayu, Yoshimura, Tomoyuki, Matsuo, Jun-ichi
Ring cleavage of 3-arylcyclobutanones and successive Friedel–Crafts alkylation of methoxy- or alkyl-substituted benzene derivatives proceeded to give 3,3-diarylbutan-2-ones by activation with titanium tetrachloride.
First Total Synthesis of (±)-Rhodoconferimide Synthesis (IF 2.650) Pub Date : 2017-11-06 Pandhade, Kailas R., Argade, Narshinha P.
Starting from vanillin and dimethyl maleate, a concise and efficient racemic total synthesis of the potent antioxidant marine natural product (±)-rhodoconferimide has been carried out via the Wittig reaction, catalytic hydrogenation, selective brominations, and imide formation. An appropriate regioselective double bromination of the aromatic ring was a key step in the synthesis.
Oxidative Functionalization of Cyclic N-Arylamines with Nitromethane and TMSCN Using the T-HYDRO/t-BuOK System Synthesis (IF 2.650) Pub Date : 2017-11-06 Rao, Gunda Ananda, Periasamy, Mariappan
Tertiary cyclic N-arylamines react with nitromethane in the presence of the tert-butyl hydroperoxide (T-HYDRO)/t-BuOK system to give β-nitroamines in up to 90% yield. When TMSCN is used in place of nitromethane, α-aminonitriles are obtained in up to 96% yield. The method is suitable for several unactivated cyclic arylamine substrates. These transformations are rationalized considering the formation of the corresponding iminium ion intermediates via an initial electron transfer process.
p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles Synthesis (IF 2.650) Pub Date : 2017-10-25 Politanskaya, Larisa, Tretyakov, Evgeny
A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent yields is reported. The heart of the proposed method consists of conversion of a Me3Si–C≡C– moiety into a MeC(=O)– group in the presence of p-toluenesulfonic acid (p-TSA) passing a stage of ethynylaniline formation. The reaction is metal-free, proceeds under mild conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity.
One-Pot Assembly towards ω-Substituted Arylbiurets from Aromatic Amines, Potassium Cyanate, and Glacial Acetic Acid Synthesis (IF 2.650) Pub Date : 2017-10-23 Min, Xiangting, Liu, Jianhui, Dong, Yawen, Hussain, Mustafa
A novel, simple, and highly efficient method has been designed for the synthesis of ω-substituted arylbiurets in a one-pot reaction. The primary features of this protocol include readily available starting materials, an easy work-up procedure, and yields of 51 to 87%. ω-Substituted arylbiurets can be selectively prepared with an excess of potassium cyanate (KOCN). However, use of an excess of glacial acetic acid (AcOH) switches the reaction towards the formation of N-monosubstituted urea.
An Efficient Fe/H2O Medium in situ Reduction and Cyclization Reaction for the Synthesis of Pyrazolo[3,4-a]acridin-10-one and Pyrazolo[4,3-a]acridin-10-one Derivatives Synthesis (IF 2.650) Pub Date : 2017-10-20 Xu, Hui, Li, Lei, Lin, Cong, Kou, Wang, Ling, Zhi, Xu, Zhongyun, Rong, Liangce
An efficient and simple method for the synthesis of pyrazolo[3,4-a]acridine and pyrazolo[4,3-a]acridine derivatives directly form nitro compounds by in situ reduction and cyclization reaction under Fe/H2O medium is reported. Compared to amino compounds, nitro compounds are more stable and easier to obtain. In addition, because iron is a nontoxic, inexpensive, and environmentally friendly reductant, this method is especially suitable for organic synthesis. The other advantages of this process are cheap raw materials, less pollution, and wide substrate range.
Asymmetric Synthetic Strategies of (R)-(–)-Baclofen: An Antispastic Drug Synthesis (IF 2.650) Pub Date : 2017-10-20 Ramesh, Perla, Suman, Devatha, Reddy, Koti Siva Nagi
Baclofen is an antispastic drug used as a muscle relaxant in the treatment of the paroxysmal pain of trigeminal neuralgia, spasticity of the spinal cord and cerebral origin. Baclofen resides biological activity exclusively in its (R)-(–)-enantiomer. In this review, various asymmetric synthetic strategies for (R)-(–)-baclofen are described.
A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis Synthesis (IF 2.650) Pub Date : 2017-10-19 Amador, Adrian G., Sherbrook, Evan M., Lu, Zhan, Yoon, Tehshik P.
A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.
Synthesis of Chiral Thiourea-Thioxanthone Hybrids Synthesis (IF 2.650) Pub Date : 2017-10-19 Mayr, Florian, Mohr, Lisa-Marie, Rodriguez, Elsa, Bach, Thorsten
Four different 1-aminocyclohexanes bearing a tethered thioxanthone group in the 2-position were prepared. The synthesis commenced with the respective N-protected β-amino acids, the carboxyl group of which was employed for the introduction of the thioxanthone moiety. After construction of the thioxanthone and protecting group removal, the conversion of the amino group into the respective thiourea was accomplished by treatment with N-3,5-bis(trifluoromethyl)phenyl isothiocyanate and yielded the title compounds in which the thioxanthone resides in different spatial positions relative to the thiourea motif. Overall yields varied between 20–35%.
Synthesis of 4-Aryl-3-arylthio-3,4-dihydroquinolin-2(1H)-ones via Cyclization of N-Arylcinnamamides with N-Thiosuccinimides Synthesis (IF 2.650) Pub Date : 2017-10-19 Ren, Hexiang, Zhang, Ming, Zhang, Aiqin
cis-4-Aryl-3-arylthio-3,4-dihydroquinolin-2(1H)-ones were synthesized via electrophilic sulfenylation and cyclization of N-arylcinnamamides with N-arylthiosuccinimides in the presence of boron trifluoride etherate. The cis-products were obtained with high stereoselectivity.
One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant Synthesis (IF 2.650) Pub Date : 2017-10-19 Shang, Xian-Xing, Vu, Huu-Manh, Li, Xu-Qin
A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc)2] and assisted by water. PhI(OAc)2 was used as the sole oxidant and water was a crucial additive. Our preliminary mechanistic investigations suggest that a water-involved, iodine(III)-promoted sequential oxidation of 2-arylindoles, which was terminated by an interesting Grob-type fragmentation of a fused tricyclic precursor, might be the main components of this one-pot transformation.
Selective Synthesis of 2- and 7-Substituted Indole Derivatives via Chelation-Assisted Metallocarbenoid C–H Bond Functionalization Synthesis (IF 2.650) Pub Date : 2017-10-19 Vorobyeva, Daria V., Osipov, Sergey N.
Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid functionalization of indole derivatives under chelation-controlled metal catalysis.
Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones Synthesis (IF 2.650) Pub Date : 2017-10-12 Bian, Chen-Yu, Li, Dan, Shi, Qian, Mei, Guang-Jian, Shi, Feng
An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.
New Efficient Synthesis of 2-Thioxo-2,3-dihydropyrimidin-4(1H)-ones from Baylis–Hillman Adducts Synthesis (IF 2.650) Pub Date : 2017-10-12 Chen, Xiuhua, Zhong, Ying, Zhao, Zhigang, Huang, Gang
Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes, which reacted with carbon disulfide at 40 °C to produce isothiocyanates. The reaction of these isothiocyanates with primary amines provided thiourea intermediates, which in the presence of potassium carbonate or sodium methoxide were converted into 2-thioxo-2,3-dihydropyrimidin-4(1H)-ones in good yields.
Controlled and Efficient Stereoselective Synthesis of Oxindole-Appended 1-Aza-1,3-butadiene Derivatives via a One-Pot Buchwald–Hartwig Amination/Elimination Strategy Synthesis (IF 2.650) Pub Date : 2017-10-12 Lingam, Kandapalam Arun Prasath, Amutha, Periyasamy, Yuvaraj, Paneerselvam, Selvakumar, Kodirajan
The enamine-free, stereoselective synthesis of oxindole-appended 1-aza-1,3-butadienes with an electron-withdrawing-group at the 3-position has been achieved in good yields from (Z)-β-bromo-substituted Morita–Baylis–Hillman (MBH) adducts of oxindoles via a one-pot Buchwald–Hartwig amination/elimination strategy. The versatility of the (Z)-β-bromo MBH adducts of oxindoles was further demonstrated by the formation of π-conjugated oxindole derivatives in typical palladium-catalysed coupling reactions.
Palladium-Catalyzed One-Pot Synthesis of N-Sulfonyl, N-Phosphoryl, and N-Acyl Guanidines Synthesis (IF 2.650) Pub Date : 2017-10-12 Qiao, Guanyu, Zhang, Zhen, Huang, Baoliang, Zhu, Liu, Xiao, Fan, Zhang, Zhenhua
An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N-sulfonyl-, N-phosphoryl-, and N-acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.
Copper-Catalyzed Synthesis of Aryl Thioamides from Aryl Aldehydes and Tetramethylthiuram Disulfide Synthesis (IF 2.650) Pub Date : 2017-10-12 Zeng, Meng-Tian, Wang, Min, Peng, Han-Ying, Cheng, Yu, Dong, Zhi-Bing
A novel and convenient method for the synthesis of aryl thioamides from aryl aldehydes and tetramethylthiuram disulfide (TMTD) without the use of sulfurating reagent was explored. In the presence of CuI and di-tert-butyl peroxide (DTBP), various aryl thioamides were prepared with good to excellent yields, tetramethylthiuram disulfide as thioamide source is essential for this transformation. The protocol features broad substrate scope, nice yields, operability and commercially available and inexpensive raw materials, showing its practical synthetic value in organic synthesis.
Mild, Efficient, and Regioselective Synthesis of Diiodophenylboronic Acid Derivatives via Metal–Iodine Exchange of 5-Substituted 1,2,3-Triiodoarenes Synthesis (IF 2.650) Pub Date : 2017-10-11 Al-Zoubi, Raed M., Ibdah, Abdellatif, Al-Jammal, Walid K., Al-Zoubi, Mazhar S., Almasalma, Ahmad A., McDonald, Robert
Unique 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives have been synthesized via regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodoarenes. The regioselectivity of the reaction per se is remarkably controlled by the nature of the C5 substituent providing the desired diiodophenylboronic acids in moderate to good yields and with high site selectivity. The diiodophenylboronic acids were then examined for in vitro antimicrobial activity against four strains of bacteria Micrococcus luteus (ATCC 9341), Bacillus cereus (ATCC 11778), Escherichia coli (ATCC 25922), and Serratia marcescens (ATCC 27117) and one fungal strain Candida albicans using well diffusion assay and dilution method. It indicated that 5-fluoro-2,3-diiodophenylboronic acid possesses the most potent antibacterial and antifungal activity with MIC of 2.6 mg/mL for M. luteus and C. albicans. This report discloses a one-step protocol to access hitherto unknowns 2,6-diiodophenylboronic acid and 2,3-diiodophenylboronic acid derivatives that is scalable, good in scope, no chromatography is needed, and these compounds are difficult to prepare by other means.
Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles Synthesis (IF 2.650) Pub Date : 2017-10-11 Cao, Chengyao Kimmy, Sheng, Jinyu, Chen, Chao
Developing versatile methodologies to construct various nitrogen-containing heterocycles is a crucially significant part of contemporary organic chemistry. This review summarizes recent developments on the formation of nitrogen-containing heterocycles triggered by diaryliodonium salts. Diaryliodonium salts, as electrophilic arylating agents in the presence of catalytic copper salts, can react with nitriles to give N-arylnitrilium cations, which are highly reactive species. These species can efficiently react with nucleophiles, including C-, N- and O-nucleophiles, to give the corresponding products. This strategy is not only efficient and convenient, but also enables the synthesis of diverse nitrogen-containing heterocycles such as quinolines, quinazolines, and phenanthridines.
Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multisubstituted Imidazoles Synthesis (IF 2.650) Pub Date : 2017-10-10 Pardeshi, Sachin D., Sathe, Pratima A., Vadagaonkar, Kamlesh S., Melone, Lucio, Chaskar, Atul C.
A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively. The use of inexpensive copper sulfate as a catalyst, readily available starting materials, and Celite-free workup makes this protocol economically viable. Multisubstituted imidazoles were obtained in moderate to good yields with significant functional group tolerance and high regioselectivity.
Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones Synthesis (IF 2.650) Pub Date : 2017-10-09 Miao, Maozhong, Xu, Huaping, Luo, Yi, Jin, Mengchao, Chen, Zhengkai, Xu, Jianfeng, Ren, Hongjun
The catalyst-free Nazarov cyclization of aryl allenyl ketones under thermal condition is developed. Various densely functionalized 2,3-dihydroindanones or indenones are readily produced in moderate to excellent yields. Significantly, this procedure features high functional group tolerance and exclusive regioselectivity. The resulting substituted 2,3-dihydroindanones can be conveniently converted into valuable conjugated benzofulvene building blocks.
α-Selective Glycosylation of 3,6-O-o-Xylylene-Bridged Glucosyl Fluoride Synthesis (IF 2.650) Pub Date : 2017-10-09 Motoyama, Atsushi, Arai, Tomoki, Ikeuchi, Kazutada, Aki, Kazuya, Wakamori, Shinnosuke, Yamada, Hidetoshi
A 1,2-cis-(α)-selective glycosylation has been developed. An ortho-xylylene group bridged between 3-O and 6-O of d-glucosyl fluoride, which straddles the β-face of the pyranose ring, hinders the approach of glycosyl acceptors from that face. The determination of the three-dimensional structure of the bridged glucosyl fluoride, the optimization process of the reaction conditions oriented toward kinetic control to realize the high α-selectivity, and the scope of the reaction are described.
Organocatalytic Enantioselective Vinylogous Henry Reaction of 3,5-Dimethyl-4-nitroisoxazole with Trifluoromethyl Ketones Synthesis (IF 2.650) Pub Date : 2017-10-04 Jafari, Ehsan, Kundu, Dipti S., Chauhan, Pankaj, Gajulapalli, V. P. Reddy, von Essen, Carolina, Rissanen, Kari, Enders, Dieter
The enantioselective vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole with trifluoromethyl ketones employing a bifunctional squaramide organocatalyst has been developed. A series of isoxazole bearing trifluoromethyl-substituted tertiary alcohols, 2-substituted (R)-1,1,1-trifluoro-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ols, were obtained under these mild reaction conditions in good yields and moderate to good enantioselectivities
Oxidative Conversion of Sulfonyl Indoles into 3-Alkylidene-2-oxindoles under Flow Chemical Conditions Synthesis (IF 2.650) Pub Date : 2017-10-04 Petrini, Marino, Chiurchiù, Elena, Rossi, Federico V., Palmieri, Alessandro
Sulfonyl indoles were converted into 3-alkylidene-2-oxindoles using NCS as the sole reagent under flow chemical conditions. The conjugated oxindole derivatives were generally obtained as E stereoisomers in moderate to satisfactory yields. The transformation entails the oxidation of the indole ring by NCS followed by elimination of arylsulfinic acid in order to install the exocyclic unsaturation.
A Facile Access to trans-3-Styryl-4-hydrazinocyclopentenes via Palladium-Catalyzed Ring Opening of Diazanorbornenes with (Z)-β-Bromostyrenes/2,3-Dibromohydrocinnamic Acids Synthesis (IF 2.650) Pub Date : 2017-10-04 Saranya, S., Chand, S. Sarath, Gopalan, Greeshma, Jijitha, V., Radhakrishnan, K. V.
trans-3-Styryl-4-hydrazinocyclopentenes have been synthesized via palladium-catalyzed desymmetrization of diazanorbornenes with (Z)-β-bromostyrenes. The reaction also works well with (Z)-β-bromostyrenes generated in situ from 2,3-dibromohydrocinnamic acids. The synthesized hydrazinocyclopentenes provide an easy route towards synthetic intermediates of many scaffolds of biological potential.
Studies Towards the Synthesis of (+)- and (–)-Anisomycin and Their Analogues Synthesis (IF 2.650) Pub Date : 2017-10-04 Ajay, Sama, Shaw, Arun K.
Anisomycin shows potent biological activity and it has attracted much attention since its isolation in 1954, with around 13 total syntheses and 20 formal syntheses, and also two reports concerning analogues of anisomycin, reported to date. The present review highlights all of these synthetic approaches (around 35) to the total or formal synthesis of anisomycin along with its isomers and analogues.
Computer-Aided Insight into the Relative Stability of Enamines Synthesis (IF 2.650) Pub Date : 2017-10-04 Castro-Alvarez, Alejandro, Carneros, Héctor, Costa, Anna M, Vilarrasa, Jaume
Venerable aldol, Michael, and Mannich reactions have undergone a renaissance in the past fifteen years, as a consequence of the development of direct organocatalytic versions, mediated by chiral amines. Chiral enamines are key intermediates in these reactions. This review focuses on the formation of enamines from secondary amines and their relative thermodynamic stability, as well as on the reverse reactions (hydrolysis). Experimental results and predictions based on MO calculations are reviewed to show which enamine forms may predominate in the reaction medium and to compare several secondary amines as organocatalysts.
Small Molecules as Long-Wavelength Fluorophores: Push-Pull Substituted 4-Alkoxy-1,3-thiazoles Synthesis (IF 2.650) Pub Date : 2017-09-26 Habenicht, Stefanie H., Rohland, Philip, Reichel, Jeaninne, Biver, Tarita, Minei, Pierpaolo, Jakobi, Dörthe, Pucci, Andrea, Weiß, Dieter, Beckert, Rainer, Görls, Helmar
A series of donor-π-acceptor (D-π-A) substituted 4-hydroxythiazoles have been synthesized. Electron-donating groups (4-methoxyphenyl and 4-dimethylaminophenyl) were installed in the 5-position of the thiazole; thiophene/pyridine-bridged acceptors (formyl groups and their Knoevenagel condensation products) were placed in the 2-position. The influence of D-π-A character on the photophysical properties and electronic structure was investigated by means of UV/Vis and fluorescence spectroscopy.
Scalable Synthesis of Hydrido-Disiloxanes from Silanes: A One-Pot Preparation of 1,3-Diphenyldisiloxane from Phenylsilane Synthesis (IF 2.650) Pub Date : 2017-09-26 Buonomo, Joseph A., Eiden, Carter G., Aldrich, Courtney C.
A simple, one-pot, and high-yielding synthesis of 1,3-diphenyldisiloxane is presented. The preparation of similar symmetrical disiloxane materials is also accomplished with this same protocol. This mechano-chemical procedure is efficient and highly scalable, furnishing a convenient route to hydrido-disiloxanes from widely accessible commercially available silanes.
A Rh(III)-Catalyzed Cascade C–H Functionalization/C(sp3)–C(sp3) Formation/Cyclization Reaction for the Synthesis of Isoquinolinedione Derivatives Synthesis (IF 2.650) Pub Date : 2017-09-25 Bai, Peng, Huang, Kenneth L., Huang, Zhi-Zhen
A cascade C–H functionalization/C(sp3)–C(sp3) formation/cyclization reaction of N-methoxybenzamides with diazomalonates under rhodium(III) catalysis is developed for the efficient synthesis of isoquinolinedione derivatives. A plausible mechanism involving double migratory insertions of carbenes for the formation of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds by rhodium(III) catalysis is also proposed.
Facile Synthesis of Rubicenes by Scholl Reaction Synthesis (IF 2.650) Pub Date : 2017-09-25 Kawamura, Masahiko, Tsurumaki, Eiji, Toyota, Shinji
The treatment of 9,10-diphenylanthracenes with DDQ in the presence of TfOH readily gave the corresponding rubicene derivatives in good yields. The effects of oxidant, acid, substituent, and other conditions are discussed. This protocol involving the Scholl reaction is convenient for the preparation of some rubicene derivatives from conventional starting materials.
Turning the Light On: Recent Developments in Photoinduced Olefin Metathesis Synthesis (IF 2.650) Pub Date : 2017-09-21 Eivgi, Or, Lemcoff, N. Gabriel
Olefin metathesis is one of the most important methods to form carbon–carbon double bonds and has found many applications in industry and academia. The ability to initiate the reaction using external stimulus such as light, with high spatial and temporal resolution is highly advantageous and provides creative novel opportunities in organic syntheses and material sciences. This review article covers recent advances in light-activated olefin metathesis reactions from the development of novel complexes that can be initiated photochemically to recently reported applications of photoinduced olefin metathesis, as well as the bright newly emerging field of photoredox-mediated metal-free ROMP.
Recent Advances in the Synthesis of Benzimidazole Derivatives from the Oxidative Coupling of Primary Amines Synthesis (IF 2.650) Pub Date : 2017-09-21 Largeron, Martine, Nguyen, Khac Minh Huy
Benzimidazole belongs to the top five most commonly used five-membered aromatic nitrogen heterocycles among U.S. FDA approved pharmaceuticals. Over the last few years, a large number of improved synthetic strategies have been developed to construct the benzimidazole molecular framework under environmentally benign conditions. This review focuses on the use of primary amines as readily available substrates for the synthesis of benzimidazole derivatives through different types of oxidative cross-coupling reactions.
Asymmetric Organocatalytic Cascade Synthesis of Tetrahydrofuranyl Spirooxindoles Synthesis (IF 2.650) Pub Date : 2017-09-18 Trubitsõn, Dmitri, Žari, Sergei, Kaabel, Sandra, Kudrjashova, Marina, Kriis, Kadri, Järving, Ivar, Pehk, Tõnis, Kanger, Tõnis
An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.
Sixfold Peripheral Halogenation of Tribenzotriquinacenes: An Alternative Access to Useful TBTQ Building Blocks Synthesis (IF 2.650) Pub Date : 2017-09-14 Linke, Jens, Bader, Natalia, Tellenbröker, Jörg, Kuck, Dietmar
Sixfold electrophilic bromination and iodination of the molecular periphery of the bridgehead-tetramethylated tribenzotriquinacene (TBTQ) with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively, under various conditions was studied to develop an alternative preparative approach to the classical Lewis acid catalyzed bromination. Running these reactions in trifluoroacetic acid either in pure form or with chloroform as a co-solvent at elevated temperatures, or under sonication or microwave irradiation was found to give increasingly fast and efficient conversion of TBTQ to the target hexahalogenated TBTQ derivatives in excellent yields. NIS was found to be markedly more reactive than NBS, whereas N-chlorosuccimide reacted hardly. The new method was applied to the sixfold functionalization of the 4b,8b,12b-tripropyl-12d-methyl-TBTQ analogue to give the corresponding hexabromo and hexaiodo derivatives. Some sixfold C–C cross-coupling reactions of hexahalo derivatives of TBTQ were carried out in excellent yields to enlarge the three spatially orthogonal indane wings of the TBTQ core.
Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide Synthesis (IF 2.650) Pub Date : 2017-09-13 Chen, Yue-Gang, Xu, Xue-Tao, Zhang, Kun, Li, Yi-Qian, Zhang, Li-Pu, Fang, Ping, Mei, Tian-Sheng
Carbon dioxide is not only an essential component of ‘greenhouse gases’, but also an abundant, renewable C1 feedstock in organic synthesis. The catalytic incorporation of carbon dioxide into value-added chemicals to produce carboxylic acids has received enormous attention. This review summarizes recent developments in the transition-metal-catalyzed carboxylation of organic halides and their surrogates, such as aryl, vinyl, and alkyl halides and pseudohalides.
One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts Synthesis (IF 2.650) Pub Date : 2017-09-12 Ding, Weijie, Hu, Juan, Jin, Huile, Yu, Xiaochun, Wang, Shun
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO2Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton–Todd Reaction under Base-Free Conditions Synthesis (IF 2.650) Pub Date : 2017-09-12 Kaboudin, Babak, Donyavi, Atousa, Kazemi, Foad
A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton–Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.
Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls Synthesis (IF 2.650) Pub Date : 2017-09-12 Rahil, Rima, Sengmany, Stéphane, Le Gall, Erwan, Léonel, Eric
Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.
Recent Advances in Magnesium Carbenoid Chemistry Synthesis (IF 2.650) Pub Date : 2017-09-12 Kimura, Tsutomu
Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.
An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines Synthesis (IF 2.650) Pub Date : 2017-09-07 Cimarelli, Cristina, Bordi, Samuele, Piermattei, Pamela, Pellei, Maura, Del Bello, Fabio, Marcantoni, Enrico
An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally friendly cerium trichloride as catalyst and allows to obtain either the anti- or the syn-isomer of the final tetrahydroquinoline with good selectivity, by performing the reaction in solvent or solventless conditions. The scope of the reaction is expanded to the one-pot synthesis of N-alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity.
Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds Synthesis (IF 2.650) Pub Date : 2017-09-07 Liu, Qiang, Chen, Xiang-Yu, Li, Sun, Vetica, Fabrizio, Raabe, Gerhard, Enders, Dieter
An efficient strategy for the synthesis of various of α,β-unsaturated γ-amino acid esters has been established employing N-heterocyclic carbene catalyzed [4+2] cycloadditions of β-methyl enals and aromatic nitroso compounds to afford 1,2-oxazin-6-ones in good yields. A subsequent acid-catalyzed esterification under ring opening yields the γ-amino enoates in good yields.
Multicatalytic Enantioselective Borrowing Hydrogen δ-Lactonization Strategy from β-Keto Esters and Allylic Alcohols Synthesis (IF 2.650) Pub Date : 2017-09-07 Quintard, Adrien, Roudier, Mylène, Rodriguez, Jean
By combining an iron-catalyzed borrowing hydrogen of allylic alcohols with an enantioselective organocatalyzed Michael addition of β-keto esters followed by a subsequent DBU-promoted lactonization different enantioenriched δ-lactones have been synthesized with good enantioselectivities. The valuable building blocks, featuring in some cases challenging quaternary stereocenters, have been obtained with >90% ee.
Decarbonylation of Aromatic Aldehydes and Dehalogenation of Aryl Halides Using Maghemite-Supported Palladium Catalyst Synthesis (IF 2.650) Pub Date : 2017-09-06 Ajdačić, Vladimir, Nikolić, Andrea, Simić, Stefan, Manojlović, Dragan, Stojanović, Zoran, Nikodinovic-Runic, Jasmina, Opsenica, Igor M.
A facile decarbonylation reaction of a variety of aromatic and heteroaromatic aldehydes using maghemite-supported palladium catalyst has been developed. The magnetic properties of catalyst facilitated an easy and efficient recovery of the catalyst from the reaction mixture using an external magnet. It was found that the catalyst could be reused up to four consecutive catalytic runs without a significant change in activity. In addition, the catalyst was also very effective in the dehalogenation of aryl halides. This is the first report on efficient utilization of directly immobilized Pd on maghemite in decarbonylation and dehalogenation reactions.
One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones Synthesis (IF 2.650) Pub Date : 2017-09-06 Wu, Mingshu, Jiang, Jie, Zhu, Zhongxiang, Wang, Qinghe, Kong, Dulin
A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C–C, 2 × C–N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.
Recent Advances in the Chemistry of 2-Acylaziridines Synthesis (IF 2.650) Pub Date : 2017-09-06 Pankova, Alena S., Kuznetsov, Mikhail A.
This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.
Highly Selective Approach to α-Iodoketones from Aminoalkynols with Iodine Monochloride Synthesis (IF 2.650) Pub Date : 2017-08-31 Rao, Vijay V., Mirzadeh, Nedaossadat, Bhargava, Suresh, Likhar, Pravin R.
A protocol has been developed to achieve selective and direct synthesis of α-iodoketones under mild condition, from the reaction of aminoalkynols with iodine monochloride. The scope of the reaction was investigated using various aminoalkynols with iodine monochloride and the corresponding α-iodoketones were obtained selectively without forming iodocyclized and/or addition products.
Nickel-Catalyzed Cross-Coupling of Functionalized Organomanganese Reagents with Aryl and Heteroaryl Halides Promoted by 4-Fluorostyrene Synthesis (IF 2.650) Pub Date : 2017-08-30 Benischke, Andreas D., Desaintjean, Alexandre, Juli, Thomas, Cahiez, Gérard, Knochel, Paul
A catalytic system consisting of Ni(acac)2 (5 mol%) and 4-fluorostyrene (20 mol%) allows a convenient cross-coupling of functionalized organomanganese reagents with a variety of aryl and heteroaryl halides leading to polyfunctionalized diaryl- and arylheteroarylmethane derivatives.
A Practical Gram-Scale Synthesis of Acrylohydroxamic Acid Synthesis (IF 2.650) Pub Date : 2017-08-30 Hamper, Bruce C., Sullivan, Brendan T., Rath, Nigam P., Spilling, Christopher D.
Acrylohydroxamic acid, which is a useful monomer for the preparation of polymeric materials, has been prepared in a straightforward, two-step synthesis from readily available starting materials. The key steps are coupling of acrylic acid with O-tetrahydropyranylhydroxyl amine to provide protection of the hydroxylamine functionality, followed by acid cleavage of the protecting group.
Some contents have been Reproduced by permission of The Royal Society of Chemistry.
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