Synthesis of novel polyfunctional pyrrolo[2,1-a]isoquinolines based on 1,3-dipolar cycloaddition reactions

Abstract

A series of 5-substituted 8-nitroisoquinolines was synthesized based on the reaction of 5-bromo-8-nitroisoquinohne with various nucleophiles. N-Alkylation products of 8-nitroisoquinolines were shown to undergo 1,3-dipolar cycloaddition to substituted alkenes and alkynes as dipolarophiles in the presence of a base to form new polyfunctional nitro-containing pyrrolo-[2,1-a]isoquinolines and their hydrogenated analogs.