Literature DB >> 29323904

[4 + 2] Cyclization of para-Quinone Methide Derivatives with Alkynes.

Guang-Jian Mei1, Shao-Li Xu1, Wen-Qin Zheng1, Chen-Yu Bian1, Feng Shi1.   

Abstract

The first cyclization of para-quinone methide derivatives with alkynes was established by utilizing the [4 + 2] reaction of ortho-hydroxyphenyl-substituted para-quinone methides with ynones or benzyne, which efficiently constructed the scaffolds of chromene and xanthene in high yields (up to 88%). This protocol has not only fulfilled the task of developing cyclization reactions of para-quinone methide derivatives but also provided an efficient method for constructing chromene and xanthene scaffolds.

Entities:  

Year:  2018        PMID: 29323904     DOI: 10.1021/acs.joc.7b02942

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


  5 in total

1.  Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Authors:  Hongmei Qin; Qimei Xie; Long He
Journal:  RSC Adv       Date:  2022-06-06       Impact factor: 4.036

2.  In the Mists of a Fungal Metabolite: An Unexpected Reaction of 2,4,5-Trimethoxyphenylglyoxylic Acid.

Authors:  Immo Serbian; Anne Loesche; Sven Sommerwerk; Phil Liebing; Dieter Ströhl; René Csuk
Journal:  Molecules       Date:  2020-04-23       Impact factor: 4.411

3.  Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates.

Authors:  Katharina Zielke; Ondřej Kováč; Michael Winter; Jiří Pospíšil; Mario Waser
Journal:  Chemistry       Date:  2019-05-21       Impact factor: 5.236

4.  Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes.

Authors:  Yuyu Cheng; Zhiqiang Fang; Yanwen Jia; Zhongyue Lu; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2019-08-05       Impact factor: 3.361

5.  One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides.

Authors:  Junwei Wang; Xiang Pan; Quanjin Rong; Lei Zhao; Lin Zhao; Weichen Dai; Kun Zhao; Lihong Hu
Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036

  5 in total

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