SYNTHESIS OF RACEMIC 1,2,3,4-TETRAHYDROISOQUINOLINES AND THEIR RESOLUTION

Abstract

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3,4-tetrahydroisoquinolines were obtained in optically pure form (>99%ee).

Authors: E. Suna and P. Trapencieris.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (3), pp 287-300

http://link.springer.com/article/10.1007/BF02256866