[5 + 1]环法制备α-重氮-β-二酮与乙烯基硫烷合成3,6-二氢- 2h -硫吡喃

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-05-17 DOI:10.1021/acs.joc.5c00330

Yinqiao Wang, Jiaxi Xu

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引用次数: 0

摘要

以α-重氮-β-二酮和乙烯基硫烷为原料，在Cu(hfacac)2催化和[5 + 1]环化微波辐照下，以中高收率合成了功能化的3,6-二氢- 2h -硫吡喃。反应机理包括α-重氮-β-二酮生成cu -类碳化合物，乙烯基硫烷对类碳化合物的亲核攻击，以及随后的[2,3]-异位重排。该工艺是乙烯基硫烷的碳诱导扩环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of 3,6-Dihydro-2H-thiopyrans from α-Diazo-β-diketones and Vinylthiiranes via [5 + 1] Annulation

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Synthesis of 3,6-Dihydro-2H-thiopyrans from α-Diazo-β-diketones and Vinylthiiranes via [5 + 1] Annulation

Functionalized 3,6-dihydro-2H-thiopyrans are synthesized in moderate to good yields from α-diazo-β-diketones and vinylthiiranes under Cu(hfacac)₂ catalysis and microwave irradiation via [5 + 1] annulation. The reaction mechanism includes a tandem sequence of the Cu-carbenoid generation from α-diazo-β-diketones, nucleophilic attack of vinylthiiranes to the carbenoids, and subsequent [2,3]-sigmatropic rearrangement. The process is a carbene-induced ring expansion of vinylthiiranes.

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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.