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Paper | Regular issue | Vol 65, No. 6, 2005, pp.1329-1345
Published online, 12th April, 2005
DOI: 10.3987/COM-05-10365
Synthesis of 1,3,8,8a-Tetrahydro-3,8-epoxyazirino[1,2-b]isoquinolines and Their Reactions with Oxygen Nucleophiles

M. José Alves, * Nuno G. Azoia, and A. Gil Fortes

*Chemistry Department, University of Minho, Campus de Gualtar, 4700-320 Braga, Portugal

Abstract

Cycloadditions of 2H-azirines to isobenzofurans is described. The endo and exo products were obtained and were reacted with oxygen nucleophiles. Tetrahydroquinolines or benzofuranols were obtained, usually in excellent yields. Cycloaddition of the less electrophilic azirine (14) was performed at room temperature in the presence of ZnCl2. The cycloadduct was hydrolysed in the reaction conditions, but dehydration to give back the original cycloadduct was obtained in the presence of 4Å molecular sieves. The structure assigned in the literature to the product of hydrolysis of the cycloadduct (10) was rectified.