An interrupted Heyns rearrangement approach for the regioselective synthesis of acylindoles
Literature Information
Minakshi Altia, Pazhamalai Anbarasan
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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Chemical Communications

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![(1R)-N-((1R)-1-Phenylethyl)-1-[4-(tert-butyldimethylsilyloxymethyl)cyclohexyl]ethan-1-amine structure (1R)-N-((1R)-1-Phenylethyl)-1-[4-(tert-butyldimethylsilyloxymethyl)cyclohexyl]ethan-1-amine structure](https://static.chemtradehub.com/structs/672/672314-45-3-47ef.webp)
