Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reactions of isoquinoline, alkyl propiolate, and thiazolidin-2,4-dione

Abstract

The reactive zwitterionic intermediates, generated from addition of isoquinoline to alkyl propiolates, react with thiazolidin-2,4-dione to afford 3-[1-(2,4-dioxothiazolidin-3-yl)isoquinolin-2(1 H)-yl]acrylates in good yields. Using (Z)-5-arylidenethiazolidine-2,4-diones as the NH-acidic component leads to 3-{1-[( Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl] isoquinolin-2(1 H)-yl}acrylates in moderate to good yields in the absence of any catalysts under mild reaction conditions. The reaction between quinoline, ethyl propiolate, and thiazolidin-2,4-dione leads to ethyl 3-[2-(2,4-dioxothiazolidin-3-yl) quinolin-1(2 H)-yl]acrylate.