PREPARATION OF 1,7-DISUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINES

ABSTRACT

A simple procedure for the preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems. A variety of 1-substituents has been incorporated using the appropriate organometallic or activated methylene nucleophile to prepare both electron rich (7a–f) and electron deficient 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines (16, 17).