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Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis. | LitMetric

Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis.

J Org Chem

School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

Published: February 2012

AI Article Synopsis

Article Abstract

In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.

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Source
http://dx.doi.org/10.1021/jo201866cDOI Listing

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