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10.13.1.1.1.4.1.1.1 Variation 1: From (o-Aminoaryl)pyruvates [3-(o-Aminoaryl)-2-oxopropanoates]; Reissert Synthesis

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (2010287.

The prototype for indoles from α-(o-aminoaryl) ketones is the classical Reissert synthesis.[‌311‌] The acidity of a methyl group ortho to nitro on an arene 329 allows methyl deprotonation. Condensation of the resulting carbanion with diethyl oxalate using potassium ethoxide as base produces a 3-(o-nitroaryl)-2-oxopropanoate (as its potassium enolate) in which the nitro group is then reduced, sometimes without prior conversion into the 2-oxopropanoate, often after hydrolysis and isolation of the 2-oxopropanoic acid itself, to give an α-(o-aminoaryl) ketone intermediate which cyclizes in situ to the indole; in the first case shown in Scheme 115 it gives ethyl 1H-indole-2-carboxylate (330), which is the simplest example; further examples are given in Table 5.

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