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Synlett 2021; 32(06): 626-630
DOI: 10.1055/a-1327-6388
letter

Synthesis of Spirocyclopropane Oxindoles via Michael-Initiated Cyclopropanation of Pyridinium Salts with 3-Ylidene Oxindoles

Jun-Qi Zhang
a   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China
,
Yujia Gao
b   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China
,
Jinyu Song
a   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China
,
Dandan Hu
a   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China
,
Maozhong Miao
b   Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China
,
Hongjun Ren  ∗
a   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. of China
› Author AffiliationsWe gratefully acknowledge the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (2019R01005) and the launching scientific research funds from Taizhou University.
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Abstract

A Michael-initiated ring-closure reaction of pyridinium salts with arylidene oxindoles has been developed. A wide range of aryl-substituted spirocyclopropane oxindoles has been achieved in moderate to good yields (41–99%). This efficient strategy exhibits good functional group compatibility and may serve as an attractive method for the synthesis of diverse cyclopropanes.

Key words

pyridinium salts - Michael - cyclopropanation - spirocyclopropane - oxindoles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1327-6388.
  • Supporting Information


Publication History

Received: 14 October 2020

Accepted after revision: 02 December 2020

Accepted Manuscript online:
02 December 2020

Article published online:
07 January 2021

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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