An interrupted Heyns rearrangement approach for the regioselective synthesis of acylindoles

Literature Information

Publication Date 2023-10-24
DOI 10.1039/D3CC04144A
Impact Factor 6.222
Authors

Minakshi Altia, Pazhamalai Anbarasan


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Abstract

An efficient and general method for the synthesis of 2- and 3-acylindoles has been achieved with high regioselectivity from o-acylanilines and α-hydroxycarbonyl or its equivalent. The strategy involves the intramolecular trapping of an in situ generated aminoenol intermediate and an interrupted Heyns rearrangement pathway, followed by aromatization or rearrangement/aromatization. Important features include excellent regiocontrol, good functional group tolerance, operational simplicity and application to gram-scale synthesis and the synthesis of an anti-tumor agent.

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