噻唑通过NaSH的正[4 + 1]反应生成(Z)-溴异氰烯烃

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-03-21 DOI:10.1021/acs.joc.4c0269110.1021/acs.joc.4c02691

Huan Tian, John-Paul R. Marrazzo, Tish Huynh and Fraser F. Fleming*,

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引用次数: 0

摘要

在溴异氰烯烃中正式[4 + 1]添加NaSH，通过一种通用的策略提供取代噻唑，该策略提供了一系列4-或5-单取代或4,5-二取代噻唑。这种独特的组装是通过NaSH在(Z)-溴异氰烯烃上罕见的SNVπ位移实现的。这种多用途的策略解决了用异氰酸酯取代的烯烃作为唯一的吸电子基团的共轭加成物的缺乏，从而提供了一系列取代噻唑。

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Thiazoles via Formal [4 + 1] of NaSH to (Z)-Bromoisocyanoalkenes

A formal [4 + 1] addition of NaSH to bromoisocyanoalkenes provides substituted thiazoles via a versatile strategy that affords an array of 4- or 5-monosubstituted or 4,5-disubstituted thiazoles. The unique assembly is achieved by a rare S_NV_π displacement of NaSH on (Z)-bromoisocyanoalkenes. The versatile strategy addresses the dearth of conjugate additions to alkenes substituted with isocyanides as the sole electron-withdrawing group to provide an array of substituted thiazoles.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.