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Iodine-promoted metal-free synthesis of mono- / di- and tri-substituted aryl sulfides / selenides in aqueous medium Tetrahedron (IF 2.1) Pub Date : 2024-03-15 Zhixia Jing, Jianxi Du, Chengtao Wang, Keyume Ablajan
The green and efficient synthesis of mono-, dis- and tri-substituted aryl sulfides and selenides was achieved via I mediated reaction of aromatic hydrocarbons with diphenyl disulfide or diselenide. A series of C–S and C–Se coupling products were obtained in good to excellent yield in the presence of 1.0 equiv. I using water as solvent at 90 °C. Our study showed that S–S and Se–Se bonds were activated
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Application of hydrazone ligands in Chan−Lam coupling of arylboronic acids and thiols Tetrahedron (IF 2.1) Pub Date : 2024-03-14 Legen Hu, Jiaquan Wang, Kelun Cui, Lin Zheng, Chunyin Zhu
A Cu/hydrazone catalysis has been applied in the oxidative coupling of arylboronic acids and aromatic thiols for the synthesis of asymmetric diaryl sulfides. The reaction features mild conditions and readily available hydrazone ligand. It works for a wide range of arylboronic acids and thiols with good to excellent yields, exhibiting great potential of such hydrazone ligands in organic synthesis.
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Ciliatonoids D–M, highly modified limonoids from the twigs of Toona ciliata Tetrahedron (IF 2.1) Pub Date : 2024-03-14 Cui-Ping Liu, Yuan Gao, Wen-Jing Li, Cheng-Hui Xu, Qun-Fang Liu, Jian Ding, Jin-Xin Zhao, Jian-Min Yue
A new ring-intact limonoid, ciliatonoid D (), five new 7,8- limonoids, ciliatonoids E–I (–), three new 7,8--29-nor limonoids, ciliatonoids J–L (–), and a new 7,8:9,11- limonoid, ciliatonoid M (), together with eleven known limonoids were isolated from the twigs of . Their structures were established by comprehensive analyses of spectroscopic, electronic circular dichroism, single-crystal X-ray diffraction
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Expanded and contracted calixpyrroles: Insights towards syntheses and molecular recognition features Tetrahedron (IF 2.1) Pub Date : 2024-03-13 Ishfaq Ahmad Rather, Rashid Ali
In the arena of molecular recognition and sensing, the development of polypyrrolic macrocycles capable of anion chelation has gained significant attention over the last two decades. The host-guest chemistry of calixpyrroles, in particular, has led to a better understanding of the guest recognition by tailoring the size, geometry, and binding modes of the receptors. Calix[4]pyrrole (C4P), a very well-known
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Solvent-free strategy for facile synthesis and cytotoxicity evaluation of benzimidazole derivatives Tetrahedron (IF 2.1) Pub Date : 2024-03-11 Hue Thi Buu Bui, Kiep Minh Do, Quang Vinh Hong, Hieu Trong Le, Saw Yu Yu Hnin, De Quang Tran, Hieu Van Mai, Thao Thi Thach Nguyen, Trang Thi Kieu Mai, Hiroyuki Morita
This study reports a facile synthesis and the cytotoxic evaluation of –H benzimidazoles. This synthetic method made use of the condensation reaction between -phenylenediamine and benzylamine and was highlighted by its solvent-free reaction conditions and short reaction time with the use of NaSO as an inexpensive and environmentally friendly oxidizing agent. The cytotoxicity assays revealed that the
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Mn(III)-based oxidative cyclization of 2,2′-(methylene)bis(3-hydroxycyclopent-2-en-1-one)s. Formation of angular spirodihydrofurans through dispirocyclopropanes Tetrahedron (IF 2.1) Pub Date : 2024-03-09 Junpei Takayanagi, Kazuki Hisano, Hiroshi Nishino
The spirodihydrofurans, i.e., the 2′,4′-spiro[cyclopentane-1,3′-cyclopenta[]furan]-2,4′,5-triones, were produced by the Mn(III)-based oxidation of the aryl-substituted (methylene)bis(3-hydroxycyclopent-2-en-1-one)s. On the other hand, a similar reaction of alkyl-substituted (methylene)bis(3-hydroxycyclopent-2-en-1-one)s did not give the or spirodihydrofurans, but dispirocyclopropanes, i.e., the 11-alkyldispiro[4
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Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III) Tetrahedron (IF 2.1) Pub Date : 2024-03-08 Alexey V. Tkachev, Alexander M. Agafontsev, Darya V. Zubricheva, Irina Yu. Bagryanskaya, Vera D. Tikhova
A series of novel hybride chiral macrocyclic compounds is described. The macrocyclic core of the new compounds is decorated with monoterpene fragments and includes 2 imine nitrogens and 2 tertiary amine nitrogens of the N,N-piperazine linkage as well as several repeating ethyleneoxy units resembling those of crown ethers. The macrocyclic compounds are prepared in moderate preparative yield (16–31%)
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Copper-catalyzed direct oxidative amination of maleimides and quinones with formamides in the presence of an oxidant KIO3 Tetrahedron (IF 2.1) Pub Date : 2024-03-03 Yu Dong, Zhen-Zhen Peng, Lin Chen, Yue-Qin Lin, Mei-Feng Lan, Chun-Mei Wu, Zhi-Chuan Shi, Guowei Deng, Bing He
A facile, efficient, and practical method for copper-catalyzed direct amination of maleimides and quinones with formamides in the presence of an oxidant KIO has been developed. It allows a facile access to a wide range of functionalized molecules with privileged scaffolds in drugs and natural products such as maleimides and quinones. A variety of substituted 3-amino-maleimides and 2-amino-quinones
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Ever-evolving helicene chemistry: Synthesis, structure and properties of novel helicenes and related molecules Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Ken Kamikawa
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Natural product-inspired molecules for covalent inhibition of SHP2 tyrosine phosphatase Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Weida Liang, Aaron D. Krabill, Katelyn S. Gallagher, Christine Muli, Zihan Qu, Darci Trader, Zhong-Yin Zhang, Mingji Dai
Natural products have been playing indispensable roles in the development of lifesaving drug molecules. They are also valuable sources for covalent protein modifiers. However, they often are scarce in nature and have complex chemical structures, which are limiting their further biomedical development. Thus, natural product-inspired small molecules which still contain the essence of the parent natural
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Biradical pincers involving two phenylene, biphenylene or terphenylene arms: Evidence for approach of two terminal nitroxides Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Rika Uesugi, Rina Takano, Takayuki Ishida
Four new pincer-type bisnitroxides, -CH{CHO-(-CH)-N(O•)-Bu} (abbreviated as and for = 2 and 3, respectively; for = 1 (known)), and -CH{CHO-(-CH)-(-CH)–N(O•)-Bu} ( and for = 2 and 3, respectively) were prepared, where -xylylenedioxy was chosen as a hinge and phenylene, biphenylene, and terphenylene were selected as an arm. The crystallographic analysis clarified the intramolecular proximity of the two
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Ratiometic fluorescent detection of Au(III) and fluorescent “turn-off” identification of Cu(II)/Hg(II) with a coumarin-based probe Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Junqiang Xu, Hao Wang, Xinhang Fang, Yuting He, Weibing Zhang, Youjun Yang, Junhong Qian
A coumarin-based fluorescent probe CHA functionalized with a 2-hydrazone pyridine unit displayed different photophysical responses to Au, Cu and Hg. It exhibited ratiometric fluorescent response to Au, whereas remarkable fluorescence “turn-off” response to Cu/Hg in aqueous solution. Au and Cu respectively induced clear blue-shift and red-shift in the absorption maximum, while Hg had little impact on
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Computational study on the reaction mechanism of phosphine-catalyzed hydroboration of propiolonitriles: With cyano group or not? Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Yanhui Wen, Yingchun Gu, Xuening Fei, Jiajia Kang, Guanglin Li, Lei Zhang
Density functional theory calculations have been performed to address the detailed mechanism of phosphine-catalyzed hydroboration of propiolonitriles. The mechanism with the cyano participation was hindered by an inaccessible free-energy barrier of 42.3 kcal/mol, while the conventional one without the cyano participation was identified to be plausible. The involved elementary steps include nucleophilic
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A facile heterogeneous catalytic approach for one-pot synthesis of fused benzoxazinones using Cuβ zeolite and Evaluation of biological activities Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Suchitha Dasu, Krishna Sai Gajula, Vasu Amrutham, Murali Boosa, Ramulamma Madasu, Madhuri Lekkala, Sai Balaji Andugulapati, Narender Nama
A simple heterogeneous catalytic process has been established for the single-step synthesis of fused benzoxazinones, quinazolinones, and thiadazines through Markownikoff's hydroamination followed by intramolecular cyclization using Cuβ zeolite. The probability and limitations of this catalytic approach were explored using various substrates. The efficiency and feasibility of scaling up the current
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Alkali-promoted transition-metal-free oxidative condensation of biomass-derived furfural and alcohols Tetrahedron (IF 2.1) Pub Date : 2024-03-02 Yanfang Zhu, Yajun Wang, Xuran Xu, Guo-Ping Lu
The oxidative condensation of furfural (FUR) with alcohols is considered to be an effective approach for the preparation of liquid transport fuel precursors. In this work, the transition-metal-free oxidative condensation of FUR with alcohols has been introduced, which is achieved by NaOBu-promoted hydrogen auto-transfer, aerobic dehydrogenation and aldol condensation under atmospheric atmosphere. C3–C10
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Total synthesis of natural alkaloids Schwarzinicines A-D Tetrahedron (IF 2.1) Pub Date : 2024-03-02 K. Annapurna, A. Venkat Narsaiah
Naturally occurring vasorelaxant alkaloids of 1,4-diarylbutanoidphenethylamines were synthesized successfully. Synthesis started from commercially available veratraldehyde, vanillin and piperonal. The important reactions involved in this synthesis are Corey-Fuchs, Eschweiler-Clarke, Henry reaction and lithium mediated carbon-carbon bond formation.
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A novel low-cytotoxicity fluorescent probe applied to monitor pH in vivo and in vitro Tetrahedron (IF 2.1) Pub Date : 2024-03-01 Jiayu Hu, Zhihua Chen, Jingjing Li, Lulu Zhang, Jincheng Zhu, Chengyu Wang, Lei Cui, Kewen Zheng
Environmental pH plays an irreplaceable role in both cellular processes and production, and anomalous pH changes within cells may lead to various diseases. To tackle this issue, we designed and synthesized the novel low-cytotoxicity fluorescent probe called . The probe incorporates 1,8-naphthalimide as the fluorescence emitter, 1-methylpiperazine as the pH-sensitive moiety, and utilizes 3-aminopropyltriethoxysilane
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Copper-mediated astatination of 211At-labelled prostate-specific membrane antigen probes in the presence of basic salts Tetrahedron (IF 2.1) Pub Date : 2024-03-01 Shigeki Watanabe, Yuto Kondo, Ichiro Sasaki, Yasuhiro Ohshima, Hiroyuki Kimura, Noriko S. Ishioka
Highly toxic alpha emitting radionuclide, astatine-211 (At) labelled compounds have great potential as therapeutic radiopharmaceuticals in the targeted alpha therapy (TAT). Previously we have reported the usefulness of copper (Cu)-mediated radiobromination and radioiodination via boronic acid precursors for the synthesis of Br/I-labelled prostate-specific membrane antigen (PSMA) inhibitors which are
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An updates: Oxidative aromatization of THβC to β-carbolines and their application for the β-carboline alkaloids synthesis Tetrahedron (IF 2.1) Pub Date : 2024-03-01 Sunil Gaikwad, Lucia Kováčiková, Priyanka Pawar, Milind Gaikwad, Andrej Boháč, Bhaskar Dawane
This review is an informative and constructive resource for researchers interested in the synthesis of -carbolines. It provides a comprehensive overview of the various synthetic pathways used between and for the aromatization of tetrahydro -carbolines (THC) to -carbolines (C). The focus is on recent advancements in oxidation, decarboxylation, dehydrogenation, and aromatization techniques using various
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The chemistry of disorazoles and structure-activity relationships: An update Tetrahedron (IF 2.1) Pub Date : 2024-02-29 Christian P. Bold, Karl-Heinz Altmann
The disorazoles are a family of 26- to 32-membered macrodiolides of mixed non-ribosomal peptide and polyketide origin that show exceptional cytotoxic activity. Of the 39 different disorazoles that have been isolated so far, total syntheses have been described for three family members, namely the non-symmetrical disorazole A and the symmetrical disorazoles B and C. With the exception of the first total
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Progress in the synthesis of polyoxamic acids Tetrahedron (IF 2.1) Pub Date : 2024-02-28 Bhagirath Limbani, Smritilekha Bera, Dhananjoy Mondal
Polyoxamic acid is a crucial part of polyoxins, which are a family of naturally occurring nucleoside peptide antibiotics and, inhibits chitin synthase from Candida albicans as potential antifungal agents. The biological activity of polyoxins is closely linked to the presence of polyoxamic acid moiety in the framework of the molecule. With three contiguous chiral centers, polyoxamic acid can exist in
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Side-chain engineering of thiazolo[5,4-d]thiazole-based medium bandgap polymer donors for efficient polymer solar cells Tetrahedron (IF 2.1) Pub Date : 2024-02-28 Jiwei Kuang, Rulin Hao, Jiyong Deng, Kai Zhang, Wenhong Peng, Rong Jiang, Qiang Tao, Weiguo Zhu
Two novel polymer donors PBF-STTz and PBSiCl-STTz based on benzo [1,2-:4,5-’]dithiophene (BDT) and thiazolo[5,4-]thiazole (TTz) with alkythiol side chain and different heteroatoms (F, Cl, Si) modification were designed and synthesized. Both polymers show the similar and strong absorption within the range of 300 nm–650 nm. By incorporation the Cl atoms, Si alkyl chains and thioalkyl chains, the deeper
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Expedite synthesis of the pentasaccharide corresponding to the cell wall O-polysaccharide of Proteus penneri O80 strain Tetrahedron (IF 2.1) Pub Date : 2024-02-28 Puja Bag, Samim Sahaji, Anup Kumar Misra
Synthesis of a -glucuronic acid containing acidic pentasaccharide repeating unit corresponding to the cell wall -polysaccharide of O80 has been successfully achieved in very good yield by stereoselective sequential glycosylations of judiciously functionalized monosaccharide intermediates. Exclusive (1 → 2)- glycosylation was achieved using a combination of copper(II) bromide and tetra--butylammonium
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Catalyst-free light-mediated polyene cyclization Tetrahedron (IF 2.1) Pub Date : 2024-02-27 Shrijana Bhattarai, Arjun Kafle, Scott T. Handy
Polyene cyclization reactions are highly efficient and unique biomimetic transformations that yield complex polycyclic molecules from their acyclic precursors. Various cation-mediated and radical-mediated synthetic methods have been developed to obtain highly diastereoselective cyclizations, along with the use of visible-light in the recent years. In this paper, we report a visible-light-mediated,
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Florisil as an efficient reagent for deprotection of tert-butyl carbamates, carbonates and esters Tetrahedron (IF 2.1) Pub Date : 2024-02-24 Cheng-Hang Liu, Mengyang Xu, Qiyun Luo, Ziyan Wang, Wenyue Tan, Xingzeng Zhao, Xiaodong Jia
Florisil (magnesium polysilicate) is an efficient and eco-friendly reagent for the deprotection of -butyl carbamates, carbonates, and ethers. Moderate to excellent yields could be achieved in the presence of other acid-sensitive groups. The separation of products is easy, and Florisil can be recycled several times without observing a decrease in yields.
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Free radical-promoted direct C–H silylation of pyrrolo[2,3-d]pyrimidine derivatives with hydrosilanes Tetrahedron (IF 2.1) Pub Date : 2024-02-23 Mingrui Liu, Ning Li, Qingbo Zhu, Zhuo Zhang, Min Liu, Zhengtong Mao, Xingxian Zhang
A transition metal-free direct C–H silylation of pharmaceutically relevant pyrrolo[2,3-]pyrimidine (7-DAPs) derivatives with hydrosilanes has been developed via a radical reaction. This protocol provides the divergent silylated 7-DAPs in moderate to good yields with good regioselectivity. The protocol features operational simplicity, broad substrate scope and the use of safe and readily available LPO
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Electrochemical C–H phosphorothiolation of indolizines with thiocyanate and phosphite in one pot Tetrahedron (IF 2.1) Pub Date : 2024-02-22 Chenglong Feng, Haochen Wang, Yuanbin She, Meichao Li, Zhenlu Shen
A facile and practical protocol for C–H phosphorothiolation of indolizines using thiocyanate as the sulfur source and phosphite as the phosphorylated reagent has been developed. A broad range of substrates were well tolerated and the desired products were obtained in moderate to excellent yields. Moreover, the reaction involved electrochemical thiocyanation of indolizines and a chemical process to
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Catalyst-free, one-pot synthesis of N,N-di(α-amino aryl ketones) from aryl glyoxals and aryl amines in presence of guanidine as a source of nitrogen Tetrahedron (IF 2.1) Pub Date : 2024-02-22 Hossein Mehrabi, Mina Hajipour
Three-component reaction between aryl glyoxals, aryl amines, and guanidine afforded ,-di (-amino aryl ketone) derivatives. This method include two C–N bonds formation in a one-pot and single synthetic step in neutral and simple reaction conditions. All reactions were conducted in EtOH as solvent at reflux conditions without using any catalyst, and the stable products were obtained in high yields. The
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Selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their N1-substituted analogues via Pd(II)-catalyzed cascade annulation of o-aminobenzoic acids with CO, ammonium acetate and aldehydes Tetrahedron (IF 2.1) Pub Date : 2024-02-22 Xiaopeng Zhang, Qiuyang Pang, Dan Liu, Guisheng Zhang
A range of 2,3-dihydroquinazolin-4(1)-ones and their 1-substituted analogues have been selectively prepared mostly in moderate to excellent yields through Pd(II)-catalyzed one-pot annulation of -aminobenzoic acids with CO, ammonium acetate and aldehydes. This protocol features with simple raw materials and operation, low catalyst loading and cost, high step economy & efficiency, good product diversity
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Understanding selectivity of nucleophilic addition to β-formyl-α-haloenoates: A synthetic and theoretical investigation Tetrahedron (IF 2.1) Pub Date : 2024-02-22 Ilya A. Tyumentsev, Igor A. Ushakov, Anton V. Kuzmin, Alexander Yu Rulev
The reactions of β-formyl-α-haloenoates with nitrogen-centered nucleophiles are described. DFT calculations have been used to better understand what factors influence and determine the chemo- and regioselectivity of the nucleophilic addition of amines to such systems. The easy synthetic approaches to the functionally substituted enoate derivatives including tertiary dehydroamino acid esters and furan-2(5)-ones
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Synthesis of Spiro[isoxazolidino[4,5-f]indolizidine-8,3′-oxindole], Spiro[indolizidine-1,3′-oxindoles], Indolo[2,3-a]quinolizidines and their anti-α-glucosidase activity Tetrahedron (IF 2.1) Pub Date : 2024-02-20 Punlop Kuntiyong, Artid Buaphan, Jitnapa Sirirak, Sasipa Booranamonthol, Phongsathon Khlongkhlaeo, Kittisak Thammapichai, Sucharat Sanongkiet
In diastereoselective synthesis of indolo [2,3-]quinolizidine and spiro [indolizidine-1,3′-oxindole] compounds from -glutamic acid, the dibenzylamino group was used for stereocontrol. Its subsequent removal generated unsaturated lactam moiety which provided the point for further derivatization. In particular, during Cope elimination of the dibenzylamino group the by-product -dibenzylhydroxylamine was
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A fluorescent probe for facile detection of gaseous styrene quantitatively Tetrahedron (IF 2.1) Pub Date : 2024-02-20 Shuai Peng, Mingfeng Zhang, Qingling Mo, Chenglong Zhong, Wenbin He, Weiwei Zhang, Xianfeng Hou
Styrene is a volatile and toxic compound that also has commercial value. Therefore, development of a simple and effective method for detecting styrene in air is essential. Inspired by our previous research, we developed a straightforward method for detecting styrene based on the Heck reaction. The probe detects styrene with a low detection limit (4.21 nM), rapid response (3 min), and good selectivity
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-Anderson type polyoxometalates and anhydride based polyimides: Synthesis, characterization and photovoltaic response in dye sensitized solar cells Tetrahedron (IF 2.1) Pub Date : 2024-02-20 Samina Parveen, Najla AlMasoud, Muhammad Nadeem, Ajaz Hussain, Khurshid Ayub, Muhammad Ammar, Hafiz Muhammad Asif, Taghrid S. Alomar, Zeinhom M. El-Bahy
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Asymmetric hydrogenation and transfer hydrogenation Tetrahedron (IF 2.1) Pub Date : 2024-02-20 Phannarath Phansavath, Virginie Vidal
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Ferric chloride mediated one pot synthesis and photophysical studies of isoindoloindolones Tetrahedron (IF 2.1) Pub Date : 2024-02-19 Arunava Misra, Sudipta Mondal, Mohabul Alam Mondal
We have explored a one-pot, tandem protocol for constructing a linear tetracyclic aromatic core isoindoloindolone via FeCl-mediated annulative coupling of 2-aminoacetophenones with phthalaldehyde (OPA). This report describes a detailed optimizations of the method, substrate scope, and characterization of the synthesized compounds by NMR, XRD, etc,. Spectroscopic analysis of one of the synthesized compounds
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A decade update on the promiscuity of α-amylase in organic synthesis Tetrahedron (IF 2.1) Pub Date : 2024-02-18 Sunil Dutt, Abinash Mohapatra, Shashi Pandey, Vikas Tyagi
Biocatalysis has emerged as a powerful technology in recent years to synthesize clinically valuable molecules. In this context, hydrolases have been used to catalyse various organic transformations. Among hydrolases, α-amylase has been recognized as a valuable biocatalyst for chemical processing in a benign reaction environment. Further, it has been widely accepted in natural transformations like hydrolysis
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Ceric ammonium nitrate catalyzed one-pot three-component microwave-assisted synthesis of indole-substituted fused pyrimidine and pyridine derivatives Tetrahedron (IF 2.1) Pub Date : 2024-02-18 Sharmil N. Anjirwala, Saurabh K. Patel
The study investigates the synthesis of fused pyridine and pyrimidine derivatives known for their diverse biological activities and structural versatility which serve as pivotal building blocks in organic synthesis. A series of indole-substituted cyanamide derivatives were synthesized by one-pot three-component cyclo-condensation between Indole-3-carboxaldehyde, malononitrile, and electron-rich aromatic
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Palladium catalyzed direct C–H arylation of 1,3,4-oxadiazole using ligand combination approach Tetrahedron (IF 2.1) Pub Date : 2024-02-17 Sneha Prasad Bakare, Mahendra Patil
The use of combination of readily available ligands in palladium catalyzed C–H arylation of 1,3,4-oxadiazole with iodoarenes as well as bromoarenes is reported. The combination of phenanthroline monohydrate (Phen.HO) and triphenyl phosphine (PPh) with Pd catalyst exhibited improved catalytical activity compared to a single ligand used separately in the reaction. A wide range of 2,5-diarylated-1,3,4-oxadiazoles
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Synthesis of highly functionalized dihydroquinolinones via a tandem benzylation/intramolecular C–N coupling strategy Tetrahedron (IF 2.1) Pub Date : 2024-02-17 Pei-Sen Gao, Chang-Wang Pan, Yan Sui, Hui-Xian Ye, Cheng Liu, Dong-Sheng Liu, Wen-Tong Chen
This study reported a tandem strategy on sequential base-controlled benzylation/Pd-catalyzed secondary amide arylation for one-pot synthesis of highly functionalized hydroquinolin-2-ones. This strategy involves creation of 3 bonds, 1 ring, and 1 quaternary carbon center while synthesizing diverse 3-cyano substituted hydroquinolin-2-ones in 41–83% yields.
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Aminopyridinium ylides from pyrano[3,4-c]pyran-7-ium salts: Synthesis and structure Tetrahedron (IF 2.1) Pub Date : 2024-02-15 Alexander А. Chekunov, Konstantin F. Suzdalev, Valery V. Tkachev, Alina V. Krachkovskaya, Leonid D. Popov, Sergey M. Aldoshin, Pavel A. Galenko-Yaroshevsky, Yuri V. Tovkach
The reaction of the bicyclic polyfunctional electrophilic system – 1-ethoxy-5-methyl-3,8-diphenyl-1-pyrano[3,4-]pyran-7-ium perchlorate with heterocyclic and aromatic acid hydrazides leads to the corresponding N-aminopyridinium ylides . The reaction conditions have been optimized and a mechanism for the formation of the ylides has been proposed.
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Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction Tetrahedron (IF 2.1) Pub Date : 2024-02-15 Elizaveta Karchuganova, Sofiia Martynova, Stanislav Kalinin, Andrea Angeli, Dmitry Dar'in, Daniella Vullo, Claudiu T. Supuran, Olga Bakulina
Sulfamide was desymmetrized by a reaction with aldehydes to give -sulfamoylimines. The latter reagents were successfully introduced into diastereo- and chemoselective transformation with cyclic anhydride using the Castagnoli-Cushman reaction to give unprotected -sulfamoyl tetrahydroisoquinolonic (THIQ) acids under simple metal-free protocol. Thereby, the first general approach to the direct assembly
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Tociliatonoid B-E, novel limonoids from Toona ciliata var. yunnanensis Tetrahedron (IF 2.1) Pub Date : 2024-02-10 Wei-Hua Wang, Cai-Ping Li, Wei Yang, Jin-Run Dong, Fa-Zhong Yang, Si-Da Xie, Ping Zhao, Guo-Lei Zhu
Four new limonoids, tociliatonoid B-E (–) were obtained from the EtOAc extract of the twigs and leaves of var. . Their structures were elucidated through comprehensive spectroscopic and X-ray crystallographic analysis. Compounds – are rare limonoids which feature unusual 3-substituted 1,5-dihydro-2-pyrrol-2-one or maleimide ring moiety at C-17 and Compound possess an aldehyde group at C-4.
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Amino-containing donor-acceptor biaryls with lactone bridging units as three-state halochromic pi-expanded coumarins Tetrahedron (IF 2.1) Pub Date : 2024-02-10 Courtney E. Westlund, Aya G. Abdrabbo, Aaron M. Bruckbauer, Deidra L. Gerlach, Tyler J. Doyon, Daniel K. Unruh, Eric W. Reinheimer, Bart J. Dahl
This report describes the synthesis and study of two new amino-containing donor-acceptor lactone-bridged biaryls as pi-expanded, or benzannulated, coumarins based on the 6H-benzo[]chromen-6-one (benzo[]coumarin) structural unit. These fluorescent and planar compounds exhibit strong intramolecular charge transfer (ICT) through the conjugated biaryl unit via a diethylamino donor on one arene and either
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Synthetic approach to the construction of unsymmetric pyridyl-1,2,4-triazine complexants Tetrahedron (IF 2.1) Pub Date : 2024-02-10 Eric A. Agyei, Jesse D. Carrick
Efforts toward further closure of the nuclear fuel cycle are contingent, in part, on chemoselective removal of the minor An from Ln within spent nuclear fuel. Liquid-liquid extraction has been demonstrated as an effective vehicle to further irradiate daughter nuclides of the minor An to products with shorter half-lives, lower radiotoxicity, and diminished contribution to heat load. Strategic synthetic
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Synthesis and cancer cell cytotoxicity of 2-heteroaryl-4-(4-heteroaryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes Tetrahedron (IF 2.1) Pub Date : 2024-02-09 Katarina Magdalenić, Felien Morlion, Steven De Jonghe, Leentje Persoons, Dominique Schols, Charlotte Grootaert, John Van Camp, Matthias D'hooghe
The natural product curcumin is often presented as a source of inspiration in the field of drug development because of its therapeutic diversity and safety for human consumption. However, although curcumin indeed shows an interesting profile in terms of biological activity, its low oral bioavailability, poor stability and unclear mechanism of action considerably weakens its case as a marketable drug
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Structure revision of lagunamide C to odoamide by total synthesis and biological evaluation Tetrahedron (IF 2.1) Pub Date : 2024-02-08 Kaduki Hagimoto, Shunya Tojo, Toshiaki Teruya, Masahito Yoshida, Hideo Kigoshi
We have accomplished the total synthesis of the putative structure of lagunamide C and revised its structure to be the related analog odoamide. Asymmetric allylation of the chiral aldehyde, followed by olefin cross metathesis successfully provided the key aliphatic acid moiety, which was coupled with the peptide moiety by ynamide-mediated esterification leading to a cyclization precursor. Finally,
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Assembly of tetracoordinated organoboron complexes from 8-aminoquinoline, aryltrifluoroborates and acylating reagents via three-component cascade reactions Tetrahedron (IF 2.1) Pub Date : 2024-02-08 Siyi Ding, Mengmeng Liu, Qiaohuan Lv, Zongcheng Miao, Liang Xu
The traditional synthetical routes towards -diaryl tetra-coordinated boron complexes usually involved the use of organometallic reagents, rendering these methods to be sensitive to air and water. Herein, we report a three-component synthetic strategy for such complexes. 8-Aminoquinolines are used as the precursor of -chelated ligands, while potassium aryl trifluoroborates (ArBFK), which are chemically
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Enantioselective Friedel-Crafts alkylation of indoles with trifluoropyruvates catalyzed by chiral Cu(II) complex bearing binaphthyl-proline hybrid ligands Tetrahedron (IF 2.1) Pub Date : 2024-02-08 Chao Yao, Jiaqi Hou, Qihang Cai, Yaoqi Chen, Chao Wang, Jiemian Liang, Zilin Jiao, Lin Li, Yue-Ming Li
A mild and efficient catalyst system for asymmetric Friedel-Crafts alkylation of indoles with trifluoropyruvates was reported. The chiral ligands took the advantages of both the proline and the binaphthyl moieties, and the in situ prepared Cu(II) catalyst showed good substrate tolerance in the reactions. Indoles bearing different substituents could be tolerated, and the desired products could be obtained
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Cu(I)-based chiral catalysts bearing binaphthyl-Proline hybrid ligands and their application in enantioselective Friedel-Crafts reactions of indoles with isatins Tetrahedron (IF 2.1) Pub Date : 2024-02-07 Chao Wang, Zilin Jiao, Jiaqi Hou, Jiahui Li, Tianxu Yu, Shibo Yu, Qihang Cai, Chao Yao, Yue-Ming Li
Highly enantioselective Friedel-Crafts reactions of indoles with isatins were realized using chiral Cu(I) catalyst bearing BINOL and proline-based electronically and sterically tunable chiral O–N–N tridentate ligands. Such catalyst system showed excellent performance in enantioselective Friedel-Crafts alkylation of different indoles, and a series of 3-indolyl-3-hydroxyoxindoles were obtained in high
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Synthesis of functionalized 3-amino-pyrrolidine-2,5-diones through an aliphatic acid silver mediated oxidative post-GBB modification reaction Tetrahedron (IF 2.1) Pub Date : 2024-02-07 Xiang Wang, Yue Sun, Meng-Yuan Wang, Jing-Ru Zou, Zeng-Yun Tian, Lei-Ming Huo, Xin-Gang Xie, Guo-Xin Wang, Xing Huo
The efficient synthesis of a range of biologically significant functionalized 3-aminopyrrolidine-2,5-dione derivatives was achieved from -fused imidazole derivatives (GBB(Groebke-Blackburn-Bienaymé) reaction products) through structural rearrangement by the treatment of aliphatic acid silver salt. The reaction features wide substrates scope, exceptionally mild conditions, moderate-to-good yields and
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Trifluoromethyl N-acylhydrazones: A versatile trifluoromethyl building blocks for construction of trifluoromethylated nitrogen-containing compounds Tetrahedron (IF 2.1) Pub Date : 2024-02-06 Zhoubin Deng, Ke-Hu Wang, Yuyu Lv, Yuanyuan Ren, Yuxiu Zhou, Danfeng Huang, Junjiao Wang, Yulai Hu
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Visible-light-promoted Meerwein 3,4-diarylation of maleimides with electron-deficient diazonium salts Tetrahedron (IF 2.1) Pub Date : 2024-02-06 Alisa D. Kharlamova, Anton S. Abel, Victoria E. Gontcharenko, Alexei D. Averin, Irina P. Beletskaya
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Synthesis of meta- and para-benziporphyrinoids and their organometallic complexes Tetrahedron (IF 2.1) Pub Date : 2024-02-06 Bharti Yadav, Ravikanth Mangalampalli
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Flexible synthesis of phosphorus(V)-substituted 1,3,4-thiadiazoles and pyridazines Tetrahedron (IF 2.1) Pub Date : 2024-02-05 Alexander Komkov, Mikhail Kozlov, Igor Zavarzin, Yulia Volkova
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Regioselective synthesis of new EWG-Bearing 3-benzoyl-2-phenylbenzofurans by one-pot intramolecular acylation/thermal cyclization of phosphoranes and their CB1 antagonist activity Tetrahedron (IF 2.1) Pub Date : 2024-02-05 Michela Begala, Michele Mancinelli, Rafaela Mostallino, Maria Paola Castelli, Giovanna Lucia Delogu
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One-pot synthesis of 1,3-diazaheterocycles via hydroxylamine hydrochloride activation of anthranilamide/phenylenediamines and DMF derivatives Tetrahedron (IF 2.1) Pub Date : 2024-02-03 Baji Baba Shaik, Sachin Balaso Mohite, Sangh Partap, Vishal Kumar, Srinivas Vangara, Muhammad Dabai Bala, Parvesh Singh, Rajshekhar Karpoormath