Synthesis of 3-Substituted Tetrahydroisoquinolines by Acid- Catalyzed Cyclization of P-Toluenesulfonamides of N-Benzyl Aminoacetaldehyde Derivatives

PONZO, VL; KAUFMAN, TS

CANADIAN JOURNAL OF CHEMISTRY, REVUE CANADIENNE DE CHIMIE

NRC Press

Lugar: Toronto; Año: 1995 vol. 73 p. 1348 - 1356

The acid-catalyzed cyclization of p-toluenesulfonamides of N-benzyl aminoacetaldehyde, or their acetalic counterparts, usualLy yields 1 ,2-dihydroisoquinolines. However, cyclization of intermediates bearing a substituent ato the carbonyl group affords 3-substituted 2-p-toluenesulfonyl tetrahydroisoquinolin-4-ol derivatives, capable of further transformation into the related 1 ,2,3 ,4-tetrahydroisoquinolines.