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通过5-碘三唑的溶剂导向发散反应合成双环[3.1.0]己烷和环戊并吡唑骨架

Access to Bicyclo[3.1.0]hexane and Cyclopenta[]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles.

作者信息

Barashkova Xenia A, Gevondian Avetik G, Latyshev Gennadij V, Kotovshchikov Yury N, Bezzubov Stanislav I, Lukashev Nikolay V, Beletskaya Irina P

机构信息

Chemistry Department, M. V. Lomonosov Moscow State University, 1/3 Leninskiye Gory, Moscow 119991, Russia.

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy pr. 31, Moscow 119991, Russia.

出版信息

Org Lett. 2024 Nov 15;26(45):9625-9630. doi: 10.1021/acs.orglett.4c03082. Epub 2024 Nov 6.

Abstract

Divergent access to bicyclo[3.1.0]hexane and cyclopenta[]pyrazole scaffolds bearing azole and azine units has been developed. The approach involves intramolecular cyclization of 5-iodo-1,2,3-triazoles acting as stable diazoimine precursors with concomitant noncatalytic (3 + 2)-cycloaddition. The choice of solvent allows control of the outcome of the cascade transformation. The developed procedure is simple and cost-efficient and allowed important heterocycles to be obtained in one-pot with various functional groups.

摘要

已开发出一种不同的方法来合成带有唑和嗪单元的双环[3.1.0]己烷和环戊并[ ]吡唑骨架。该方法涉及作为稳定重氮亚胺前体的5-碘-1,2,3-三唑的分子内环化,同时进行非催化(3 + 2)环加成反应。溶剂的选择可以控制级联转化的结果。所开发的方法简单且具有成本效益,能够在一锅反应中获得带有各种官能团的重要杂环化合物。

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