Literature DB >> 25562802

Silver-mediated radical cyclization of alkynoates and α-keto acids leading to coumarins via cascade double C-C bond formation.

Kelu Yan1, Daoshan Yang, Wei Wei, Fen Wang, Yuanyuan Shuai, Qiannan Li, Hua Wang.   

Abstract

A novel and convenient silver-mediated radical cyclization method for the synthesis of coumarin derivatives via the direct difunctionalization of alkynoates with α-keto acids through double C-C bond formation under mild conditions has been developed. This new method is highly efficient and practical, and the starting materials are readily prepared. The present method should provide a useful strategy for the construction of coumarin motifs.

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Year:  2015        PMID: 25562802     DOI: 10.1021/jo502474z

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  9 in total

Review 1.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

2.  Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Authors:  Arghya Banerjee; Zhen Lei; Ming-Yu Ngai
Journal:  Synthesis (Stuttg)       Date:  2018-12-12       Impact factor: 3.157

3.  Catalytic C-H Bond Activation and Knoevenagel Condensation Using Pyridine-2,3-Dicarboxylate-Based Metal-Organic Frameworks.

Authors:  Rampal Pandey; Durgesh Singh; Neha Thakur; Krishna K Raj
Journal:  ACS Omega       Date:  2021-05-12

4.  One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8.

Authors:  Teppei Sasaki; Katsuhiko Moriyama; Hideo Togo
Journal:  Beilstein J Org Chem       Date:  2018-02-05       Impact factor: 2.883

5.  KI-catalyzed oxidative cyclization of α-keto acids and 2-hydrazinopyridines: efficient one-pot synthesis of 1,2,4-triazolo[4,3-a]pyridines.

Authors:  De-Suo Yang; Juan Wang; Peng Gao; Zi-Jing Bai; Dong-Zhu Duan; Ming-Jin Fan
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

6.  A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile.

Authors:  Selçuk Eşsiz
Journal:  RSC Adv       Date:  2021-05-20       Impact factor: 3.361

7.  ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline.

Authors:  Keke Huang; Jia-Ni Li; Guanyinsheng Qiu; Wenlin Xie; Jin-Biao Liu
Journal:  RSC Adv       Date:  2019-10-17       Impact factor: 4.036

Review 8.  Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds.

Authors:  Angela Stefanachi; Francesco Leonetti; Leonardo Pisani; Marco Catto; Angelo Carotti
Journal:  Molecules       Date:  2018-01-27       Impact factor: 4.411

Review 9.  Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials.

Authors:  Melita Lončarić; Dajana Gašo-Sokač; Stela Jokić; Maja Molnar
Journal:  Biomolecules       Date:  2020-01-16
  9 in total

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