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肉桂基叠氮化物与乙烯基砜的级联反应直接生成二氢吡咯并吡唑杂环。

A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles.

作者信息

Carlson Angela S, Petre Alexandru M, Topczewski Joseph J

机构信息

Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, MN 55455, United States.

出版信息

Tetrahedron Lett. 2021 Mar 16;67. doi: 10.1016/j.tetlet.2021.152860. Epub 2021 Feb 3.

DOI:10.1016/j.tetlet.2021.152860
PMID:34054152
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8153508/
Abstract

This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%-72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

摘要

本报告描述了由烯丙基叠氮化物和甲基乙烯基砜直接合成二氢吡咯并吡唑杂环化合物的方法。该产物是由一个操作简单的复杂串联反应生成的,芳构化是伴随消除步骤的结果。多种叠氮化物可参与此反应(12个例子),所需产物的分离产率为51%-72%。最后,通过在吡咯烷中加热产物可除去乙烯砜基团。

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