Tandem [4C + 2C] cyclization reaction of α-acetyl-α-oxo ketene dithioacetals and acrylonitrile: A straightforward synthesis of polysubstituted cyclohex-3-enones

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-04-25 DOI:10.1080/00397911.2025.2496972

Xiaobo Zhao (Funding acquisition Writing – original draft) , Zixuan Cha (Investigation) , Xinyue Liu (Investigation) , Jiaqin Liu (Investigation) , Yuheng Zhang (Investigation) , Haifeng Yu (Funding acquisition Project administration Writing – review & editing)

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引用次数: 0

Abstract

In the investigation, the tandem (Michael addition/nucleophilic cyclization/Michael addition reactions) [4C + 2C] cyclization reaction of α-acetyl-α-oxo ketene dithioacetals as four-carbon synthons and acrylonitrile as two-carbon components is developed under mild reaction conditions. In the presence of 1 equivalents of t-BuOK, the tandem [4C + 2C] cyclization reaction of α-acetyl-α-oxo ketene dithioacetals and acrylonitrile efficiently occur to polysubstituted cyclohex-3-enones in 60–72% yields. Twenty-four new products were synthesized and characterized by NMR, FTIR, HRMS and X-ray crystallography. The approach exhibits fascinating features such less expensive, efficient and operationally convenient, ease of scale-up.

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α-乙酰基-α-氧酮二硫缩醛与丙烯腈的串联[4C + 2C]环化反应：多取代环己烯酮的直接合成

在温和的反应条件下，以α-乙酰基-α-氧基烯酮二硫缩醛为四碳合子，丙烯腈为二碳组分，进行了串联（Michael加成/亲核环化/Michael加成反应）[4C + 2C]环化反应。在1个当量的t-BuOK存在下，α-乙酰基-α-氧基烯酮二硫缩醛与丙烯腈的串联[4C + 2C]环化反应高效地生成了多取代环己烯-3-烯酮，收率为60-72%。合成了24个新产物，并用核磁共振、红外光谱、质谱和x射线晶体学对其进行了表征。该方法具有成本低、效率高、操作方便、易于扩展等令人着迷的特点。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.