Issue 26, 2022

Synthesis of 3C-alkylated active methylene substituted 2H-indazole derivatives via sequential ring opening of donor–acceptor cyclopropanes and reductive cyclization reaction

Abstract

A concise sequential protocol is developed to synthesize 3C-alkylated active methylene substituted 2H-indazole derivatives via a nucleophilic ring opening reaction (NRO) of o-nitro donor–acceptor cyclopropanes (DACs) with primary arylamines catalyzed by Ni(ClO4)2·6H2O followed by a SnCl2·2H2O-mediated intramolecular reductive cyclisation. The di-ester functionality can be transformed into the corresponding monoesters, acids, alcohols and amides that form the core units of important biologically active molecules.

Graphical abstract: Synthesis of 3C-alkylated active methylene substituted 2H-indazole derivatives via sequential ring opening of donor–acceptor cyclopropanes and reductive cyclization reaction

Supplementary files

Article information

Article type
Communication
Submitted
13 Apr 2022
Accepted
12 Jun 2022
First published
13 Jun 2022

New J. Chem., 2022,46, 12456-12460

Synthesis of 3C-alkylated active methylene substituted 2H-indazole derivatives via sequential ring opening of donor–acceptor cyclopropanes and reductive cyclization reaction

A. K. Sahu, S. Biswas, S. K. Bora and A. K. Saikia, New J. Chem., 2022, 46, 12456 DOI: 10.1039/D2NJ01801B

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