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银催化高炔丙基磺酰胺与对醌甲基化物的串联环化/1,6-共轭加成:一种合成多种3-二芳基甲基取代二氢吡咯的方法。

Silver-Catalyzed Cascade Cyclization/1,6-Conjugate Addition of Homopropargyl Sulfonamides to -Quinone Methides: An Approach to Diverse 3-Diarylmethine Substituted Dihydropyrroles.

作者信息

Shirsath Sachin R, Ghotekar Ganesh S, Bahadur Vir, Gonnade Rajesh G, Muthukrishnan M

机构信息

Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.

出版信息

J Org Chem. 2020 Dec 4;85(23):15038-15050. doi: 10.1021/acs.joc.0c01922. Epub 2020 Oct 29.

Abstract

A silver-catalyzed cycloisomerization/1,6-conjugate addition of homopropargyl sulfonamides to -quinone methides to access diverse diarylmethine substituted dihydropyrroles has been disclosed. The reaction pathway involves an intramolecular cascade cyclization of homopropargyl sulfonamides to generate a highly reactive dihydropyrrole intermediate in situ followed by conjugate addition with -quinone methides. This method provides an efficient and scalable route for the synthesis of 3-diarylmethine substituted dihydropyrroles, in one pot.

摘要

已公开了一种银催化的高炔丙基磺酰胺与醌甲基化物的环异构化/1,6-共轭加成反应,用于合成多种二芳基甲基取代的二氢吡咯。反应途径涉及高炔丙基磺酰胺的分子内级联环化,原位生成高活性的二氢吡咯中间体,随后与醌甲基化物进行共轭加成。该方法为一锅法合成3-二芳基甲基取代的二氢吡咯提供了一条高效且可扩展的路线。

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