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Paper | Regular issue | Vol 87, No. 10, 2013, pp.2023-2029
Published online, 10th September, 2013
DOI: 10.3987/COM-13-12789
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


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 SnCl22H2O and thus this one-pot strategy also permitted the expeditious synthesis of indolines in good yield.