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通过对甲苯磺酰基-1,2,3-三唑的无金属脱磺酰基烷基化反应合成β-三唑啉酮

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of -tosyl-1,2,3-triazoles.

作者信息

Pati Soumyaranjan, Almeida Renata G, da Silva Júnior Eufrânio N, Namboothiri Irishi N N

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.

Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, CEP 31270-901, Belo Horizonte, MG, Brazil.

出版信息

Beilstein J Org Chem. 2021 Mar 31;17:762-770. doi: 10.3762/bjoc.17.66. eCollection 2021.

Abstract

Desulfonylative alkylation of -tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and -tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new functionalized 1,2,3-triazoles.

摘要

本文报道了在无金属条件下,-对甲苯磺酰基-1,2,3-三唑的脱磺酰基烷基化反应,生成β-三唑基烯酮。本研究涵盖了从环状1,3-二羰基化合物和-对甲苯磺酰基三唑一步合成具有新取代模式的三唑,产率适中至高。我们的合成具有完全的区域选择性,经晶体学分析证实,并通过合适的机理推测进行了合理化解释。该方法为合成新型官能化1,2,3-三唑提供了一种高效、通用且直接的策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8fbf/8022205/50fa34c145cb/Beilstein_J_Org_Chem-17-762-g003.jpg

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