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Communication | Regular issue | Vol 20, No. 7, 1983, pp.1247-1254
Published online, 1st January, 1970
DOI: 10.3987/R-1983-07-1247
Solvent Effect on the Bischler-Napieralski Reaction. Synthesis of 3-Aryl-3,4-dihydroisoquinolines

Esther Domínguez and Esther Lete

*Departmento de Química, Facultad de Ciencias, Universidad del País Vasco, Apartado 450, 01080 Vitoria-Gasteiza, Spain

Abstract

The classical Bischler-Napieralski cyclization of 1,2-diaryl-ethylamides always led to neutral compounds: the 3,4,3’,4’-tetramethoxystilbene (5) and/or the triaryl substituted tetralin (6). These characteristic by-products of the Bischler-Napieralski reaction arise as a consequence of competing equilibria involving nitrilium ions. The desired 3-aryl-3,4-dihydroisoquinolines were obtained in acceptable yields when the “appropiate” nitrile was used as solvent.