Journal of Organic Chemistry 2012-02-03

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

Martyn Inman, Anna Carbone, Christopher J Moody

Index: J. Org. Chem. 77(3) , 1217-32, (2012)

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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.