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Serendipitous base catalysed condensation–heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles

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Abstract

A serendipitous discovery of a novel one-pot synthesis of 4,6-disubstituted 5-azaindoles is reported herein. In the presence of Hunig's base, various N-substituted pyrrole-2-carboxaldehydes have been efficiently transformed into their corresponding 4,6-disubstituted 5-azaindoles through an imine mediated cascade condensation–heteroannulation. The synthetic value of the methodology is established by preparing a novel chemical analogue of a cannabinoid receptor type 2 (CB2) agonist.

Graphical abstract: Serendipitous base catalysed condensation–heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles

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Article information


Submitted
17 Dec 2019
Accepted
04 Feb 2020
First published
04 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Serendipitous base catalysed condensation–heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles

P. Dudhe, K. Venkatasubbaiah, B. Pathak and V. Chelvam, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02657F

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