A novel sodium carbonate-catalyzed regioselective synthesis of pyrano[2,3-h]coumarins using a three-component reaction Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-17 Hamideh Mohamadi Tanuraghaj, Mahnaz Farahi
Mycopyranone: a 8,8ˈ-binaphthopyranone with potent anti-MRSA activity from the fungus Phialemoniopsis sp Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-17 José Rivera-Chávez, Lindsay Caesar, Juan J. Garcia-Salazar, Huzefa A. Raja, Nadja B. Cech, Cedric J. Pearce, Nicholas H. Oberlies
Progress in Intermolecular and Intramolecular Reactions of Thioamides with Diazo Compounds and Azides Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-17 Vasiliy Bakulev, Yuri Shafran, Wim Dehaen
Copper(I)-Catalyzed Direct C-H Trifluoromethylation of Imidazoheterocycles with Togni’s Reagent Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-17 Ruonan Wang, Jingcai Wang, Qingxuan Tang, Xin Zhao, Junfeng Wang, Yuting Leng, Yangjie Wu, Junbiao Chang, Yusheng Wu, Zhaoda Zhang, Shiwei Wang
Design and Synthesis of [1,2,4]-Triazolo Isoquinoline Derivatives via 1, 3-Dipolar [3+2] Cycloaddition: Reaction of Azomethine Imine with Ethyl Cyanoformate as Unknown Protocol Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-17 K. Jones M. Swapnaja, Satyanarayana Yennam, Murthy Chavali
Indium(III) chloride catalyzed synthesis of novel 1H-pyrazolo[1,2–b]phthalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under solvent-free condition Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-16 Amol Maruti Jadhav, Sandip Gangadhar Balwe, Jong Su Kim, Kwon Taek Lim, Yeon Tae Jeong
First synthesis and further derivatization of furo[3,2-c]pyrazol-6-ones Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-14 Clément Jacob, Clemens Lamberth
An ESIPT-Based Fluorescent Probe for Hg2+ in Aqueous Solution and Its Application in Live-Cell Imaging Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-14 Jun Tang, Hui Wu, Shuai Yin, Yifeng Han
Hofmann Rearrangement of Primary Carboxamides and Cyclic imides using DCDMH and Application to the synthesis of Gabapentin and its Potential Peptide Prodrugs Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-14 Jashuva V.P Katuri, Kuppuswamy Nagarajan
Total synthesis based modification of Benzoquinone Ansamycin Antibiotics: C8 Diversification of C5-C15 Fragments Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-12 Longlong Jin, Rentao Zhang, Zhi Zhang, Chuancai Bian, Xiaoming Yu
A facile synthesis of novel 9-substituted 2,3,4,9-tetrahydro-1H-xanthen-1-ones Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-11 Dariusz Deredas, Bartosz Łągiewka, Waldemar Maniukiewicz
First stereoselective total synthesis of antibiotic macrolide Berkeleylactone F Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-11 Mopuri Sudhakar Reddy, Gembali Manikanta, Palakodety Radha Krishna
Catalytic and metal-free intramolecular hydroalkoxylation of alkynes Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-11 Alexandre Jean, Jacques Rouden, Jacques Maddaluno, Michaël De Paolis, Jérôme Blanchet
Synthesis of Chiral allene Moiety from Morita-Baylis-Hillman adduct of isatin derivatives via Claisen Rearrangement Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-11 Vadivel Vaithiyanathan, Ganesan Ravichandran, Vijayakumar Thirumailavana
A novel carbocatalytic hydride transfer strategy for efficient reduction of structurally different aldehydes and ketones in water Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-11 Vijai K. Rai, Suhasini Mahata, Smita R. Bhardiya, Prashant Shukla, Ankita Rai, Manorama Singh
Chichibabin pyridinium synthesis Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-08 Akiho Imura, Nao Tanaka, Toyonobu Usuki
Chichibabin pyridine synthesis involves the reaction of three aldehydes and ammonia to form 2,3,5-trisubstituted pyridines. This study examined the synthesis of tetrasubstituted pyridinium from aldehydes and an amine hydrochloride in the presence/absence of Pr(OTf)3. Important insights into the reaction mechanisms of Chichibabin pyridinium synthesis were proposed through the investigation of reaction intermediates along with quantitative GC-MS analysis.
Synthesis of 1,3-dioxo-substituted allenes via copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos by controlling the sequence of adding substrates Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-09 Chulong Liu, Yunxiang Weng, Xiaobao Zeng, Weiping Zheng, Xinyan Wang, Yuefei Hu
A novel direct synthesis of 1,3-dioxo-substituted allenes was developed by copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos. It was a sequence of adding substrates-controlled method and the desired products were synthesized chemoselectively by adding α-oxo-alkyne terminally.
Application of deuterated THENA for assigning the absolute configuration of chiral secondary alcohols Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-09 Jakapun Soponpong, Kulvadee Dolsophon, Chawanee Thongpanchang, Anthony Linden, Tienthong Thongpanchang
The structure of a constrained bicyclic chiral derivatizing agent (CDA), 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid, THENA 1, was modified by replacing both exo-methylene protons with deuterium atoms. The modified CDA, THENA-d22, could be used to assign the absolute configuration of chiral secondary alcohols with good reliability. Compared with THENA, the multiplicity of the methylene proton signals in the 1H NMR spectra of THENA-d2 derivatives is less complicated and the new CDA thus offers simpler NMR spectra for data interpretation.
Synthesis of novel 1,2,3-triazole based polycarboxylic acid functionalised ligands for MOF systems Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-09 Yonas Belay, Louis-Charl Coetzee, D. Bradley G. Williams, Alfred Muller
Copper catalysed click reactions are excellent tools to generate various 1,2,3-triazole linked polytopic aromatic carboxylates. The general reaction route involves protection of the carboxylates before proceeding with the click reaction. These polycarboxylate azoles are conveniently prepared for potential utility as novel key building blocks for metal organic frameworks. In one case, the ligand crystallises into a solid structure containing 1D, 2D and 3D features, based on a zigzag 1D structure, a ‘chicken mesh’-like 2D structure and a 3D structure with very well-defined channels.
Novel and efficient synthesis of triazolobenzodiazepine analogues through the sequential Ugi 4CR-click-N-arylation reactions Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-07 Mohammad Sadegh Asgari, Mehdi Soheilizad, Parviz Rashidi Ranjbar, Bagher Larijani, Rahmatollah Rahimi, Mohammad Mahdavi
An efficient approach for the synthesis of N-alkyl-2-aryl-2-(6-oxo-4H-benzo[f], , triazolo[1,5-a], diazepin-5(6H)-yl)acetamides is described. The protocol involves Ugi four-component reaction of 2-bromobenzoic acid, propargylamine, aldehydes and isocyanides followed by in situ sequential click reaction of azide ion with triple bond and N-arylation reaction to afford desired products in good to excellent yields.
Palladium-catalyzed reductive Heck reaction of α,β-unsaturated alkenes and cycloalkyl iodides Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-07 Zhenwei Liu, Shanshan Wei, Apeng Liang, Jingya Li, Dapeng Zou, Yusheng Wu, Yangjie Wu
The palladium catalyzed reductive Heck reactions of unactivated cycloalkyl iodides with α,β-unsaturated alkenes have been developed. A number of hydrocycloalkylated alkenes were obtained in reasonable yields under the optimized conditions. The obvious advantage of this approach is that the hydride source was provided by Et3N and no other reductant or base was required in the reaction.
Enamine-azide [2+3]-cycloaddition as a method to introduce functional groups into fluorescent dyes Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-04 Nadezhda S. Baleeva, Snizhana O. Zaitseva, Konstantin S. Mineev, Anastasia V. Khavroshechkina, Marina B. Zagudaylov, Mikhail S. Baranov
Fluorescent dyes are a significant research tool with various applications in modern science. However, many experiments require the preparation of covalent dye conjugates, which is impossible without the presence of a functional group on the dye molecule. Unfortunately, the introduction of such groups is often a complicated task. Herein, we report a novel approach for the introduction of functional groups into fluorescent dyes, based on the [2+3]-cycloaddition reaction of “terminal” enamines with azides. The synthesis of such “terminal” enamines is carried out by the condensation of formamide acetals with a methyl group that is influenced by a strong electron withdrawing group. Thus, the proposed functionalization technique requires only the presence of a methyl group in the relevant position of the initial non-functionalized fluorescent dye.
Synthesis, characterization and epoxidation of hexakis-4-(2-(4-((β-methallyl)oxy)phenyl)propan-2-yl)phenoxycyclotriphosphazene Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-04 Evgeniy M. Chistyakov, Sergey N. Filatov, Pavel A. Yudaev, Vyacheslav V. Kireev
4-(2-(4-((β-Methallyl)oxy)phenyl)propan-2-yl)phenol was prepared via the reaction of methallyl chloride with bisphenol A and used for the synthesis of hexakis-4-(2-(4-((β-methallyl)oxy)phenyl)propan-2-yl)phenoxycyclotriphosphazene. It was revealed that the latter undergoes the Claisen rearrangement and can be also epoxidized by 3-chloroperbenzoic acid. The obtained epoxide was cured by a treatment with isophorone diamine. The decomposition and glass transition temperatures of cured resin were also estimated (275 and 130 °C, respectively) by DSC and TGA methods.
Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-04 Furgan Aslanoglu, Sinan Basceken, Metin Balci
A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2',1'-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesis of 4',5'-dihydro-1H,3'H-2,2'-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton.
An Improved Phosphoramidite Approach for the Chemical Synthesis of 3’,5’-Cyclic Diguanylic Acid Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-04 Andrzej Grajkowski, Mayumi Takahashi, Tomasz Kaczyński, Suresh C. Srivastava, Serge L. Beaucage
3’,5’-Cyclic diguanylic acid (c-di-GMP) plays important roles as a signaling and effector molecule in prokaryotes as well as inducing innate and adaptive immune responses in mammalian cells through activation of cell death pathways. An improved phosphoramidite method for the synthesis of c-di-GMP is reported herein. The method is based on the use of an unprecedented 5’-O-formyl ester, which can efficiently and chemoselectively be cleaved from a dinucleotide phosphoramidite intermediate to permit a 1H-tetrazole-mediated cyclocondensation reaction leading to a fully protected c-di-GMP product in a yield of 78%. The native c-di-GMP is isolated in an overall yield of 36% based on the commercial ribonucleoside used as starting material.
Stereodivergent Synthesis of Cyclic γ-Aminobutyric Acid - GABA Analogues Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-04 Andrej Ďuriš, Dušan Berkeš, Pavol Jakubec
A novel synthetic route towards two series of enantiomerically pure cyclic analogues of 2,3-cis- and 2,3-trans-γ-aminobutyric acid (GABA) was developed. The route is based on the elongation and stereodivergent manipulation of a readily accessible enantiomerically pure γ-substituted α-aminolactone. The five-step route towards the 2,3-cis-substituted GABA analogues was achieved via straightforward carbon chain extension of the lactone using a non-classical Wittig reaction followed by chemoselective reduction and a protecting group switch. The five-step route towards the 2,3-trans-substituted GABA analogues employed elongation of the same aminolactone using a Horner-Wadsworth-Emmons reaction and highly stereoselective intramolecular oxa-Michael addition as the key synthetic manipulations. Altogether this chemistry has allowed the stereodivergent preparation of a novel class of GABA analogues in two diastereomeric series.
Direct catalytic asymmetric method for the synthesis of tetrahydropyranopyrazoles through allene zwitterion chemistry Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-06 Raghupathi Mutyala, R. Venkatram Reddy, Ravikiran Donthi, V.S. Ramakrishna Kallaganti, Rajesh Chandra
The enantioselective synthesis of the tetrahydropyranopyrazole scaffold has been achieved. The quinidine catalyzed reaction of allenoates with arylidenepyrazolones proceeded with high enantio- and diastereoselectivity while the reactions of alkylidenepyrazolones were less efficient. Allene ketones also afforded tetrahydropyranopyrazole derivatives in high yields, however, with only moderate enantioselectivity. The primary adduct undergoes further functional group transformations without effecting the initially formed chiral centre.
Ferrier Reaction : The first synthesis of 2,3-unsaturated seleno-glycosides by using alkyl(aryl) hydroselenides as the nucleophile and Hf(OTf)4 as the catalyst Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-03 Peiran Chen, Yajun Ding, Saisai Guo, Xiaoying Zhang
By using Hf(OTf)4 as the catalyst, a series of 2, 3-unsaturated-Se-glucosides have been synthesized for the first time from tri-O-acetyl-D-glucal , 2,4,6-tri-O-benzyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal and ((2R ,3S)-3-acetoxy-2,3-dihydrofuran-2-yl) methyl acetate with PhSeH or alkyl(aryl) hydroselenides as the nucleophile in good yield and high anomeric selectivity.
Synthesis of a novel family of water-soluble 2H,3H-[1,3]thia- and -selenazolo[3,2-a]pyridin-4-ium heterocycles by annulation reactions Tetrahedron Lett. (IF 2.125) Pub Date : 2019-01-02 Vladimir A. Potapov, Roman S. Ishigeev, Svetlana V. Amosova, Tatyana N. Borodina
Regioselective synthesis of a novel family of water-soluble 2H,3H-[1,3]chalcogenazolo[3,2-a]pyridin-4-ium derivatives was developed based on 2-pyridinesulfenyl and -selenenyl halides and unsaturated compounds. The annulation reactions with divinyl sulfide, selenide and N-vinylpyrrolidin-2-one led to addition of the chalcogen atom to the terminal carbon of the double bond whereas the reaction with tetravinylsilane proceeded with opposite regiochemistry. Tricyclic condensed heterocycles were obtained from 2,3-dihydrofuran and cycloalkenes. The products represent novel promising scaffolds for organic synthesis and possible drug discovery.
2-Isopropylbenzimidazole and 2-methylbenzimidazole as bulky proton sources: Stereoselective protonation and application to the synthesis of γ- and δ-lactones Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-28 Aakash Sengupta, Seijiro Hosokawa
2-Isopropylbenzimidazole and 2-methylbenzimidazole have been found to be effective bulky proton sources for stereoselective protonation of chiral enolate anions. 2-isopropylbenzimidazole worked in the stereoselective protonation of the Birch reduction of chiral α, β -unsaturated imides. On the other hand, 2-methylbenzimidazole was found to be the best protonation reagent in the isomerization reaction of α, β -unsaturated imide into β, γ -unsaturated imide. The Birch reduction using 2-isopropylbenzimidazole realized a concise and stereoselective synthesis of δ -lactone 14, a sex pheromone of Macrocentrus grandii, while the isomerization reaction using 2-methylbenzimidazole was employed in the highly stereoselective synthesis of the γ -lactone intermediate in the synthesis of depsipeptide antibiotics. These bulky proton sources would be powerful tools to achieve a concise synthesis of natural products.
Stereocontrolled synthesis of the macrolactone core of neopeltolide Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-28 Andreas Meissner, Nobuhiro Tanaka, Hiroyoshi Takamura, Isao Kadota
A stereoselective synthesis of the macrolactone core of neopeltolide is described. The tetrahydropyran moiety was constructed via the intramolecular allylation of an α-acetoxy ether. A late-stage macrolactonization provided a known synthetic intermediate of neopeltolide.
A new and efficient synthesis of (3E, 8Z, 11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer Tuta absoluta Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-29 Jorge A. Cabezas
An efficient synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer moth, Tuta absoluta, was accomplished. The synthesis started with but-3-yn-1-ol and gave an overall yield of 41%.
Triptycene-scaffolded tetraphenylethylenes with irregular temperature-dependence AIE Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-29 Lijun Wang, Wenjie Li, Zhaoxia Wang, Qianfu Luo
A series of new tetraphenylethylene monomer, dimer and three-dimensional trimer based triptycene-bridged triphenylethenes has been constructed. Their structures were clearly confirmed and the irregular fluorescent behaviors at different temperatures and solvents were investigated. Results showed the new tetraphenylethylenes performed remarkable aggregation-induced emission (AIE) properties and the emission intensities are dependent on temperature and viscosity. Compared with the model tetraphenylethylene without connecting triphenylethylene, the fluorescence quantum yields of the titled triptycene-scaffolded tetraphenylethylenes in aggregation are greater than tetraphenylethylene and increased as the increasing of the triphenylethylene units.
Acid-Promoted Multicomponent Allylic Amidation towards 7-acetamido tetrahydroindole derivatives Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-29 Sayan Pramanik, Suvendu Maity, Prasanta Ghosh, Chhanda Mukhopadhyay
An acid-promoted multicomponent reaction for the direct C(sp3)−N bond formation was achieved through intermolecular allylic amidation in a one-pot operation to synthesize 7-acetamido tetrahydroindole derivatives from simple and readily available arylglyoxal monohydrates, acetonitriles, and enamines of 5,5-dimethyl-1,3-cyclohexadione (dimedone) has been developed. Here acetonitrile acts both as solvent and reagent. These tetahydroindole derivatives are formed through domino condensation of the enamines and arylglyoxals followed by annulation and allylic amidation.
Design and Synthesis of Spirobiisoxazoline Dibenzoquinone Derivatives via [3+2] Double 1,3-Dipolar Cycloaddition Reaction Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-29 K. Jones. M. Swapnaja, Satyanarayana Yennam, Murthy Chavali
“A series of novel spirobiisoxazoline dibenzoquinone derivatives were synthesized starting from 2,5-dimethoxybenzaldehyde in a six-step synthetic sequence”. The key step [3+2] double 1,3-dipolar cycloaddition of oxime chloride with allenoate was performed under mild reaction conditions using sodium carbonate at ambient temperature. This is the first innovative synthesis of Spirobiisoxazoline Dibenzoquinone system where quinone ring is alkylated to isoxazoline moiety.
Reduction of phosphine oxides to phosphines Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-30 Evgeniya Podyacheva, Ekaterina Kuchuk, Denis Chusov
The digest is devoted to the most widespread reducing agents which are used for the reduction of tertiary and secondary phosphine oxides, phospholene oxides, phospholane oxides, phosphonates, phosphinates, α- and β-hydroxy and thiomethyl phosphine oxides, α-aminophosphonates α-aminophosphine oxides. Stereoselectivity of reactions is described. Methods of stabilization of phosphines which are prone to re-oxidation by the formation of borane-adduct or metal complexes are considered.
Iron-catalyzed δ-Selective Conjugate Addition of Methyl and Cyclopropyl Grignard Reagents to α,β,γ,δ -Unsaturated Esters and Amides Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-30 Goshi Sugano, Kojiro Kawada, Masayuki Shigeta, Takeshi Hata, Hirokazu Urabe
Iron-catalyzed δ-selective conjugate addition of methyl and cyclopropyl Grignard reagents toα,β,γ, δ -unsaturated esters and amides took place in good yields to give products exclusively with cis- β, γ -olefinic bond.
Regio- and stereo-controlled synthesis of β-Xyl(1-4)Rbo-5P1-Rbo, the partial structure of O-mannosyl glycan Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-31 Takahiro Tamura, Jun-ichi Tamura
O-Mannosyl glycan is a pivotal glycan part of α-dystroglycan, which serves as a transmembrane linker connecting the intracellular cytoskeleton and extracellular matrix, such as laminin in skeletal muscle. We synthesized β-D-Xyl-(1-4)-D-Rbo-5P (1), β -D-Xyl-(1-4)-D-Rbo (2), and β -D-Xyl-(1-4)-D-Rbo-5P1-D-Rbo (3), partial structures of O-mannosyl glycan, in regio- and stereo-controlled manners, and demonstrated compatibility with the natural product.
Blue Light Photoredox Decarboxylation and Tin-Free Barton-McCombie Reactions in the Stereoselective Synthesis of (+)-Muscarine Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Victoria Rodríguez-Tzompanzi, Leticia Quintero, Dulce M. Tepox-Luna, Silvano Cruz-Gregorio, Fernando Sartillo-Piscil
Starting from a 1,2-O-isopropylidene-D-xylofuranose derivative, a non-toxic free-radical approach for the synthesis of (+)-muscarine is reported. To this end, a stereoselective allylation reaction at the anomeric position of a respective xylofuranose derivative was employed as a new synthetic strategy for the installation of the methyl group at the C-5 position of (+)-muscarine. Accordingly, the allyl group was transformed into the methyl group in three sequential steps highlighting a blue-light photoredox decarboxylation reaction. Additionally, a tin-free Barton-McCombie deoxygenation reaction of the respective C-methyl glycoside allowed the completion of this free-radical approach to (+)-muscarine.
Alkylation Reactions of Benzothiazoles with N,N-dimethylamides catalyzed by the Two-Component System under Visible Light Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Jian-Quan Weng, Wen-Xiu Xu, Xiao-Qiang Dai, Jun-Hui Zhang, Xing-Hai Liu
Eosin Y/K2S2O8 catalyzed C2-alkylation reactions of benzothiazoles with N,N-dimethylamides under visible light have been developed. The reactions completed smoothly in the presence of Eosin Y as the photocatalyst and K2S2O8 as the oxidant under solvent-free conditions in open air. This green and simple method provides an alternative route for the synthesis of C2-alkylation of benzothiazoles and tolerates a number of functional groups to afford moderate to excellent yields.
An efficient synthesis of 2-isoxazolines from α-haloketone oximes and dimethyl sulfonium salts Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Sen Zhao, Hang Wang, Shaofa Sun, Haibing Guo, Zhiyu Chen, Jian Wang, Lu Wang, Steven Liang, Gangqiang Wang
2-Isoxazolines were synthesized efficiently from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a range of 2-isoxazolines in high yields and high regioselectivity.
Synthesis of the cyclohexene segment of portimine Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Takafumi Saito, Kenshu Fujiwara, Yoshihiko Kondo, Uichi Akiba, Takanori Suzuki
The synthesis of the cyclohexene segment of portimine, a marine cytotoxin from the dinoflagellate Vulcanodinium rugosum, was achieved. The route includes an acylation/aldol reaction from 3-ethoxycyclohex-2-enone to create the C3 center, the 1,4-addition of a vinyl group at C16, the diastereoselective dihydroxylation of the vinyl group to generate the C15 center, a vinylation/dehydration sequence to set up the diene moiety, and stepwise installation of the amino-group-substituted C1 unit.
Diastereoselective Scalable Synthesis of 2,6-trans-Piperidines using an aza-Michael Reaction Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Somenath Chowdhury, Jianmin Mao, Jacek Martynow, He Zhao, Erin Duffy, Yusheng Wu, Vinay Thakur, Gopal Sirasani, Yuanqing Tang, Florine Collin, Sandra Sinishtaj, Ashoke Bhattacharjee
Highly efficient substrate and reagent controlled stereoselective synthesis of 2,6-trans-piperidine derivative (1) using an aza-Michael reaction is reported. This method was utilized to synthesize a variety of trans-piperidines on hundred-gram scales.
Pleosporalesones A–B, two unique polyketides isolated from Pleosporales sp. Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Li-Hua Zhang, Jian Bai, Dao-Jiang Yan, Ya-Nan Wang, Ya-Long Zhang, Li Li, Bing-Yu Liu, You-Cai Hu
Two unique polyketides, pleosporalesones A–B (1–2), bearing an unusual 6/6/7/6 tetracyclic ring system consisting of a chromone ring and a benzoannulated cycloheptanone ring, were isolated from the solid cultures of Pleosporales sp.. The chemical structures were elucidated by analyses of their extensive spectroscopic data, including 1D/2D NMR, ORD, CD and HR-ESI-MS, and the absolute configurations were established by comparison of their experimental circular dichroism data with those calculated. A plausible biosynthetic pathway for pleosporalesones A–B was proposed.
A Simple 1H NMR Method for Determining the σ-Donor Properties of N-Heterocyclic Carbenes Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-26 Guangrong Meng, Lazaros Kakalis, Steven P. Nolan, Michal Szostak
The σ-donor properties of NHC ligands (NHC = N-heterocyclic carbene) are essential for controlling the interaction with transition metals, and as a consequence, to determine the selectivity and reactivity of NHCs in transition-metal-catalysis. Herein, we report a simple NMR method for estimating the σ -donor properties of NHC ligands based on a straightforward H NMR measurement of ligand precursors. We present evaluation of σ -donating properties for a range of NHC ligands varied by structure and electronics that are relevant to transition-metal-catalysis. We expect that the simple measurement of σ -donating properties of NHCs, together with the known methods for evaluating sterics and π-backbonding, will enhance the understanding of the properties of NHCs in transition-metal-catalysis.
Orthoamides by selective borohydride reduction of N, N’, N’’-triacyl- and N, N’, N’’-tri(alkoxycarbonyl)-guanidines Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-27 Matthew C. Davis, Thomas J. Groshens
N, N’, N’’-Triacylguanidines and N, N’, N’’-tri(alkoxycarbonyl)guanidines were prepared and reduced with borohydride salts in a mixture of tetrahydrofuran and acetic acid to give triacyl and tri(alkoxycarbonyl) orthoamides in yields of 40–85%. However, similar reduction of N, N’, N’’-tri(t-butoxycarbonyl)guanidine did not give orthoamide but the aminal di(t-butyl) methylenedicarbamate.
Temperature Responsive Polymer-Supported TEMPO: An Efficient and Recoverable Catalyst for the Selective Oxidation of Alcohols Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-23 Tao Chen, Zhenkai Xu, Lei Zhou, Laiyu Hua, Shuo Zhang, Jiping Wang
This study aimed to combine the advantages of homogeneous catalysis and heterogeneous catalysis by immobilizing TEMPO into a water-soluble temperature responsive polymer. The supported TEMPO was water soluble and displayed excellent activity in the selective oxidation of alcohols below the LCST and can be easily recovered.
Synthesis of sulfonimide-based dendrimers and dendrons possessing mixed 1→2 and 1→4 branching motifs Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-23 Mykola Kolotylo, Volodymyr Holovatiuk, Julia Bondareva, Oleg Lukin, Vladimir Rozhkov
The synthesis of dendrimers and a chlorosulfo-dendron possessing a unique combination of 1→2 and 1→4 branching types is described. The procedure consists of a two-step preparation of 3,5-dinitrobenzene-1-sulfonyl chloride, which was used for the persulfonylation of p-toluidine and 4-(benzylthio)aniline. The obtained tetranitro compounds were reduced to the corresponding tetraamines. The latter were decorated with eight 4-toluene sulfonyl groups each to furnish the corresponding dendrimers. Oxidation of the dendrimer possessing a 4-(benzylthio)phenylene core with N-chlorosuccinimide resulted in the formation of a dendron with a sulfonyl chloride functionality at the focal point.
Synthesis of aminobenzoxazoles via simple, clean and efficient electrochemical redox reactions Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-24 Tanay Ghoshal, Vishal Nagar, Adilakshmi Vutla, Sharadsrikar Kotturi, Sasikumar Kuttappan
An efficient single step process for the construction of pharmaceutically relevant substituted aminobenzoxazoles have been described in this report. Various electrodes and electrolytes combinations have been carried out to harvest optimum coupling results. The presented C-N bond formation reaction methodology has applied for the synthesis of biologically active compounds. This methodology saves reaction steps over traditional functionalization reactions.
Metal-free synthesis of chromeno[4,3-c]pyrazol-3(2H)-one derivatives Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-24 Ashish Dhamsaniya, Shahrukh khan Safi, Pratiksha Chhatbar, Prachi Trivedi, Kaushik Pambhar, Vaibhav Mehta, Anamik Shah
An unprecedented metal-free synthesis of 4-(methylthio)chromeno[4,3-c]pyrazol-3(2H)-one is reported via sequential one-pot desulfitative [5+1] hetero-annulation. The present strategy consists of one-pot sequential, base catalysed dithioketene formation from active methylene of pyrazolone followed by methylation and [5+1] heteroannulative cyclization. The resulting substrate undergoes facile nucleophilic substitution with various amines to yield 4-(substituted-amine)-chromeno[4,3-c]pyrazol-3(2H)-one derivatives under metal free condition.
An anomalous effect of fluorine on the conformational equilibrium of 2-fluorocyclohexane-1,3-dione Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-24 Laize A.F. Andrade, Josué M. Silla, Matheus P. Freitas
Conformational stabilities of 2-halocyclohexane-1,3-diones are strongly affected by steric and dipolar effects involving the carbonyl groups and the equatorial halogen. However, 2-fluorocyclohexane-1,3-dione has been found to be mostly equatorial, because of electron delocalization in this conformer that overcomes repulsive interactions, while the other halogen derivatives perform as expected.
Synthesis of new Substituted Cylopentenone Derivatives Via a One-Pot Three-Component Reaction Between Arylglyoxals, Acetylacetone, and Amines in Aqueous Media Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-25 Nasim Tajaddini, Mahdiyeh Talebizadeh, Mohammad Anary-Abbasinejad
An efficient one-pot method for the synthesis of new substituted cylopentenone derivatives is described via reaction of arylglyoxals and acetylacetone with aliphatic amines. This reaction was carried out in aqueous media in the absence of any catalyst or promoter to produce substituted cylopentenone in high yield.
3H-Pyrroles as a platform for the catalyst-free construction of dihydropyrrolo[2,1-b]oxazoles: [4+2]-cycloaddition vs [2+3]-annulation with 1-cyano-3-hydroxyalkynes Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-21 Ludmila A. Oparina, Dmitrii A. Shabalin, Nikita A. Kolyvanov, Igor' A. Ushakov, Anastasiya G. Mal'kina, Alexander V. Vashchenko, Boris A. Trofimov
Non-aromatic pyrrole isomers, 3,3-dialkyl-2-aryl-3H-pyrroles, were reacted with 1-cyano-3-hydroxyalkynes under mild, catalyst-free conditions (20-60 oC) to regio- and stereoselectively afford (Z)-2-(dihydropyrrolo[2,1-b]oxazolylidene)acetonitriles in 62-82% yield, thus evidencing the preference for [2+3]-annulation over the [4+2]-Diels-Alder alternative. The reaction involves initial nucleophilic addition of the pyrrole moiety at the triple bond followed by tandem ring closure of an anionic intermediate.
Unnatural Tripeptide as Highly Enantioselective Organocatalyst for Asymmetric Aldol Reaction of Isatins Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-22 Kazumasa Kon, Yoshihito Kohari, Miki Murata
The development of unnatural tripeptides as highly enantioselective organocatalysts for the asymmetric aldol reaction of isatins was achieved. H-Pro-Gly-D-Ala-OH with the D-alanine residue as the C-terminal amino acid residue expressed the best enantioselectivity. The H-Pro-Gly-D-Ala-OH-catalyzed reaction of isatins gave various aldol adducts with up to 93% yield and up to 97% ee. Investigation of the transition state via DFT calculation revealed that high optical purity was realized by the D-alanine controlled steric environment.
New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-22 Bakhtar Ullah, Yuli Zhou, Jingwen Chen, Zongbi Bao, Yiwen Yang, Qiwei Yang, Qilong Ren, Zhiguo Zhang
Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative α -cyanation of N-aryltetrahydroisoquinolines (THIQs) with TMSCN, giving the corresponding products in good to excellent yields. Experimental investigations demonstrated that thiourea acts as a radical initiator by abstracting hydroxyl radical (∙OH) from tert-butyl hydroperoxide (TBHP) directly instead of non-covalent H-bonding activation. The use of thiourea as a radical initiator offers a new avenue for innovative chemical transformations in organocatalyzed radical chemistry.
“Geländer” macrocycles: synthesis, chirality and racemisation barriers Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-21 Claudia Lar, Mădălina Elena Moisă, Elena Bogdan, Anamaria Terec, Niculina Daniela Hădade, Ion Grosu, Luminiţa David, Csaba Paizs, Ioana Georgeta Grosu
A new class of axially-chiral o,o’-bridged biphenyls containing etheroxime chains was obtained in good yields by the macrocyclisation reaction of o,o’-diformylbiphenyl dioxime with several ditosylated or dibrominated reagents. In all cases the enantiomers of the compounds were separated by HPLC using a chiral column (Chiralpack IC) and the stability of the enantiomers (barriers of racemisation) was investigated employing chiral HPLC or chiral Dynamic HPLC techniques. A slight influence on the barrier to rotation was noticed when the enantiomerisation was performed in the presence of suitable alkali cations.
A simple and versatile method to synthesize N-acyl-benzotriazoles Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-21 Guillaume Laconde, Muriel Amblard, Jean Martinez
An efficient method for the synthesis of N-acyl-benzotriazoles from a wide variety of protected amino acids, as well as from compounds frequently used in drug discovery such as biotin and N-Fmoc polyethylene glycol, has been developed. The reaction of carboxylic acid derivatives with benzotriazole in the presence of T3P® yielded the corresponding N-acyl-benzotriazoles, which were obtained in high purity following a simple work-up procedure, in most cases via precipitation of the desired product in water.
A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-18 Xingquan Xiong, Chao Yi, Xu Liao, Shilin Lai
A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68–90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amount of Cu(OAc)2 in deep eutectic solvent (DES). The new synthetic method has many advantages, such as high conversion, green reaction medium, easy work-up, low cost, and environment friendly.
Metallophthalocyanine−Catalyzed Olefination of Aldehydes Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-18 Dominic L. Ventura, Scott J. Heller, Tara D. Noworyta, Kristopher C. Kijanka, Brandon M. Belz
The Wittig reaction to synthesize olefins is a very attractive method in organic synthesis. Recently, this methodology has been achieved utilizing simple metal catalysts and diazo compounds in addition to a phosphine and an aldehyde. The following work investigates the use of a variety of metallophthalocyanines (MPc’s) to catalyze Wittig-like reactions from ethyldiazoacetate. We also examine the influence of substitution on the aromatic ring of the aldehyde as well as various phosphines, arsines and antimony complexes. We have been able to exclusively synthesize the trans-olefins in excellent yields in short periods of time (1 hour).
The DFT Study on Rh-C Bond Dissociation Enthalpies of (iminoacyl)rhodium(III)hydride and (iminoacyl)rhodium(III)alkyl Tetrahedron Lett. (IF 2.125) Pub Date : 2018-12-18 Huifang Chang, Wenrui Zheng, Yuanyuan Zheng, Danfeng Zhu, Jiaoyang Wang
Rhodium transition-metal-organic cooperative catalysis, which has been intensively studied by many chemists, represents a great success in C-H bond activation because of high efficiencies and selectivities. Typically, in the reaction mechanism of aldehyde and alkene catalyzed by Rh(I) complex and 2-amino-3-picoline, two kinds of metala-cyclic transition-metal complexes of (iminoacyl)rhodium(III)hydride and (iminoacyl)rhodium(III) alkyl are generally formed. The two complexes play an important role in the overall reaction, in which the Rh-C bond formations are involved. So it is meaningful to understand the strength of Rh-C bond, which can be measured by the homolytic bond dissociation enthalpies (BDEs). To this end, we first calculated 16 relative Rh-C BDEs of Tp’Rh(CNneopentyl)RH (Tp’=hydridotris-(3,5-dimethylpyrazolyl)borate) by 19 density functional theory (DFT) methods. Furthermore, the 5 absolute Rh-C BDEs of Rh transition-metal complexes were also calculated. The results show that the B97D3 is the most accurate method to predict the relative and absolute Rh-C BDEs and the corresponding RMSE values are the smallest of 2.8 and 3.3 kcal/mol respectively. Therefore, the Rh-C BDEs of (iminoacyl)rhodium(III)hydride and (iminoacyl)rhodium(III)alkyl as well as the substituent effects were investigated by using the B97D3 method. The results indicated that the different substituents exhibit different effects on different types of Rh-C BDEs. In addition, the analysis including the natural bond orbital (NBO) as well as the energies of frontier orbitals were performed in order to further understand the essence of the Rh-C BDE change patterns.
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