Literature DB >> 21607267

Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides.

Hiroto Yoshida1, Yu Ito, Joji Ohshita.   

Abstract

ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner. This journal is © The Royal Society of Chemistry 2011

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Year:  2011        PMID： 21607267     DOI： 10.1039/c1cc11955a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Benzyne Cascade Reactions via Benzoxetenonium Ions and Their Rearrangements to o-Quinone Methides.

Authors:  Hang Shen; Xiao Xiao; Thomas R Hoye
Journal:  Org Lett       Date:  2019-03-04       Impact factor: 6.005

2.  Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.

Authors:  Yao Liu; Xiao-Bing Yu; Xiang-Mei Zhang; Qian Zhong; Li-Hua Liao; Nan Yan
Journal:  RSC Adv       Date:  2021-08-04       Impact factor: 4.036

3.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

4.  Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si.

Authors:  Hiroto Yoshida
Journal:  Chem Rec       Date:  2016-01-20       Impact factor: 6.771

5.  Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

Authors:  Eito Yoshioka; Shigeru Kohtani; Hideto Miyabe
Journal:  Molecules       Date:  2014-01-13       Impact factor: 4.411

Review 6.  Transition-Metal-Free Activation of Amide Bond by Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2018-08-27       Impact factor: 4.411

Review 7.  Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2015-07-09       Impact factor: 4.411

Review 8.  3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade.

Authors:  Maria J Matos; Eugenio Uriarte; Lourdes Santana
Journal:  Molecules       Date:  2021-11-08       Impact factor: 4.411

Review 9.  Beyond a solvent: triple roles of dimethylformamide in organic chemistry.

Authors:  Majid M Heravi; Mahdieh Ghavidel; Leyla Mohammadkhani
Journal:  RSC Adv       Date:  2018-08-03       Impact factor: 4.036
  9 in total

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