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Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of nitroallylic acetates with indoline-2-thiones

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Abstract

An efficient one-pot method has been developed for the regio- and stereoselective synthesis of thiopyran annulated indoles. It involves a base mediated cascade [3+3] annulation of indoline-2-thiones and nitroallylic acetates. The tetrahydrothiopyranoindoles which were formed in good yields and in a short reaction time could be easily transformed to triazole derivatives by taking advantage of the nitro group present in the skeleton.

Graphical abstract: Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of nitroallylic acetates with indoline-2-thiones

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Article information


Submitted
17 Sep 2019
Accepted
05 Dec 2019
First published
09 Dec 2019

New J. Chem., 2020, Advance Article
Article type
Paper

Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of nitroallylic acetates with indoline-2-thiones

P. Basu, C. Hazra, T. V. Baiju and I. N. N. Namboothiri, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ04754A

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