Reaction of <i>N</i>-Nitroso-1,2,3,4-tetrahydroisoquinolines with Base. A New Method for the Conversion of 1,2,3,4-Tetrahydroisoquinolines into 3,4-Dihydroisoquinolines

Abstract

Abstract Treatment of N-nitroso-1,2,3,4-tetrahydroisoquinoline (2a) and its 1-methyl derivative (2b) with base gave the corresponding 3,4-dihydroisoquinolines (3a and 3b). However, similar treatment of N-nitroso-1,2,3,4-tetrahydroisoquinoline-1-acetic acid (2c) gave a mixture of 3b and 1,2,3,4-tetrahydroisoquinoline-1-(α-hydroxyimino)acetic acid (4).