78283-29-1Relevant articles and documents
Indoles from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction: 4-Benzyloxyindole
Batcho, Andrew D.,Leimgruber, Willy
, p. 214 - 214 (2017/06/01)
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SYNTHESIS OF 4-SUBSTITUTED INDOLES FROM o-NITROTOLUENES
Kruse, Lawrence I.
, p. 1119 - 1124 (2007/10/02)
A facile two- or three-step transformation of o-nitrotoluenes into 4-substituted indoles is described.Treatment of o-nitrotoluenes 1 with DMF acetal, or sometimes more advantageously with tris(N,N-dimethylamino)methane, affords β-(N,N-dimethylamino)styrenes 2 which are readily converted too-nitrophenylacetaldehyde semicarbazones 3 without isolation.Reduction of either 2 or 3 affords 4-substituted indoles 4.Use of the very insoluble semicarbazones results in vastly superior yields of 4 by minimizing completing bimolecular condensation reactions during reduction.This new procedure has been applied to efficiently and conveniently prepare a series of 4-substituted indoles 4.