Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 319-324 ◽  
Author(s):  
Zhaozhan Wang ◽  
Tao Song ◽  
Yong Yang
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Biologically Active ◽  
One Pot ◽  
Mild Conditions ◽  
Wide Range ◽  
High Yields

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Molybdenum-Mediated One-Pot Synthesis of Pyrazoles from Isoxazoles

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3796-3804 ◽  
Author(s):  
Marine Rey ◽  
Stéphane Beaumont
Keyword(s):  
Bond Cleavage ◽  
Direct Synthesis ◽  
Molybdenum Complex ◽  
One Pot ◽  
One Pot Synthesis ◽  
Wide Range ◽  
Hydrolysis Of ◽  
Substituted Pyrazoles

A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho-Quinone Methides Generated In Situ

Synlett ◽  
2018 ◽  
Vol 30 (02) ◽  
pp. 189-192 ◽  
Author(s):  
Yujiro Hoshino ◽  
Kiyoshi Honda ◽  
Kenta Tanaka ◽  
Mami Kishimoto ◽  
Naoya Ohtsuka ◽  
...  
Keyword(s):  
Biologically Active ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis ◽  
Reaction Proceeds ◽  
Acidic Conditions ◽  
High Yields

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho-quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

scholarly journals Direct Sulfoxidation of Aromatic Methyl Thioethers with Aryl Halides by Copper-Catalyzed C(sp3)–H Bond Activation

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 105
Author(s):  
Runsheng Xu ◽  
Yueer Zhu ◽  
Feixiang Xiong ◽  
Suli Tong
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Aryl Halides ◽  
Biologically Active ◽  
Mild Conditions ◽  
Methyl Thioethers ◽  
High Yields

A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently synthesized in good to high yields under mild conditions. This new methodology provides an economical approach toward C(sp3)–C(sp2) bond formation.

A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one Derivatives Using Acidic Ionic Liquid [C4mim][HSO4]

2016 ◽  
Vol 69 (9) ◽  
pp. 1049 ◽  
Author(s):  
Sudesh Kumari ◽  
M. Rajeswari ◽  
Jitender M. Khurana
Keyword(s):  
Ionic Liquid ◽  
Crystal Packing ◽  
Aromatic Aldehydes ◽  
Green Solvent ◽  
One Pot ◽  
X Ray ◽  
Acidic Ionic Liquid ◽  
Green Approach ◽  
Wide Range ◽  
High Yields

A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([C4mim][HSO4]) is reported. Structures have been confirmed by spectral and X-ray studies. Crystal packing of 4b has also been reported. Green solvent, short reaction time, easy workup, and high yields are the salient features of the present protocol.

Sequential one-pot approach for the synthesis of functionalized phthalans via Heck-reduction–cyclization (HRC) reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (34) ◽  
pp. 26749-26761 ◽  
Author(s):  
Jonnada Krishna ◽  
Pedireddi Niharika ◽  
Gedu Satyanarayana
Keyword(s):  
Direct Synthesis ◽  
Practical Method ◽  
Biologically Active ◽  
Structural Motif ◽  
One Pot ◽  
Synthetic Compounds ◽  
Active Natural

An efficient and practical method is described for the direct synthesis of 1,3-dihydroisobenzofurans, an important structural motif present in biologically active natural or synthetic compounds.

Copper-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2-a]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1530-1536 ◽  
Author(s):  
Tao Guo ◽  
Shu-Lei Han ◽  
Yong-Cheng Ma ◽  
Xu-Ning Wei ◽  
Ying-Li Zhu ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Breast Cancer Cell ◽  
Functional Group ◽  
Biological Evaluation ◽  
Boronic Acids ◽  
Breast Cancer Cell Lines ◽  
One Pot ◽  
Wide Range ◽  
Antiproliferative Activities

An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2-a]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2-a]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived lung, stomach, esophageal, and breast cancer cell lines.

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1373-1377 ◽  
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Yidong Yu ◽  
Yiyong Zhao ◽  
Xiaoqiang Xie
Keyword(s):  
Functional Group ◽  
Oxidative Cyclization ◽  
Mild Conditions ◽  
Broad Scope ◽  
Oxadiazole Derivatives ◽  
High Yields

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

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