Issue 33, 2018

Synthesis of imidazopyridine-fused indoles via one-pot sequential Knoevenagel condensation and cross dehydrogenative coupling

Abstract

A simple and efficient strategy for the synthesis of imidazopyridine-fused indoles has been developed that involves one-pot sequential Knoevenagel condensation of readily available active methylene azoles with N-substituted-1H-indole-3-carboxaldehydes or N-substituted-1H-indole-2-carboxaldehydes followed by palladium-catalyzed intramolecular cross dehydrogenative coupling reaction. A series of 36 derivatives was prepared by using this strategy. The products were obtained in moderate to excellent (32–94%) yields and showed broad substrate scope with tolerance of various functional groups and was amiable for gram scale preparation without problems.

Graphical abstract: Synthesis of imidazopyridine-fused indoles via one-pot sequential Knoevenagel condensation and cross dehydrogenative coupling

Supplementary files

Article information

Article type
Paper
Submitted
20 Jun 2018
Accepted
03 Aug 2018
First published
03 Aug 2018

Org. Biomol. Chem., 2018,16, 6123-6132

Synthesis of imidazopyridine-fused indoles via one-pot sequential Knoevenagel condensation and cross dehydrogenative coupling

V. N. Shinde, S. Dhiman, R. Krishnan, D. Kumar and A. Kumar, Org. Biomol. Chem., 2018, 16, 6123 DOI: 10.1039/C8OB01449C

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