Stereochemical Aspects during Substitution Reaction of c-4-Bromo-r-1-cyano-c-3-methoxy-1, 2, 3, 4-tetrahydroisoquinoline Derivatives with Amines

Abstract

2-Acyl (or sulfonyl)-c-4-bromo-r-1-cyano-t-3-methoxy-1, 2, 3, 4-tetrahydroisoquinolines treated with primary or secondary amines are stereoselectively converted into 4-amino-1, 2, 3, 4-tetrahydroisoquinoline derivatives in high yields. The 1, 4-trans and 3, 4-trans configuration of the products has been determined by X-ray crystallography. The formation of an isoquinoline o-quinone type compound 5 is suggested as an intermediate in the reaction process.