Reaction of 1-Alkylthioisoquinolinium Salts with Active Methylene Compounds

Abstract

2-Alkyl-1-alkylthioisoquinolinium salts were readily prepared from 2-alkyl-1(2H)-isoquinolones via 2-alkyl-1(2H)-thioisoquinolones in two steps. Under mild conditions, the reaction of 2-alkyl-l-alkylthioisoquinolinium salts with active methylene compounds in the presence of sodium hydride afforded 2-alkyl-1-(substituted methylene)iso-quinolines in good yields. Pyrrolo[2,1-a]isoquinolines were synthesized by the cyclization of 2-benzyl-1-(substituted methylene)isoquinolines using acetic anhydride.