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■ Facile Synthesis of Indolines by a Tandem Nitro-reduction Aza Michael Addition Reaction

Wellington Martins Ventura, Luiz Guilherme Souza de Assis, and Jason Guy Taylor*

*Department of Chemistry, Federal University of Ouro Preto, Bauxita, ICEB, UFOP, Ouro Preto 35400-000, Brazil

Abstract

A diverse array of substrates are conveniently prepared by coupling diazonium salts to ethyl vinyl ether and subjecting the resultant aldehyde intermediate to a Wittig reaction to provide α,β-unsaturated esters with only one purification step. The cyclisation of 4-aryl-but-2-enoates is carried out in the presence of stoichiometric amounts of SnCl2∙2H2O and thus this one-pot strategy also permitted the expeditious synthesis of indolines in good yield.