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The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1'quinolizines] in high yields and with high diastereoselectivity. The Diels-Alder reactions of spiro[indoline-3,1' quinolizines] with maleic anhydride and N- phenyl maleimides successfully resulted in polyfunctionalized isoquinolinuclidine derivatives. The similar three-component reactions with quinoline resulted in the novel spiro[indoline-3,4' -pyrido[1,2-a]quinolines] in moderate to good yields.

molecular diversity

Synthesis of spiro[indoline-3,1 $$^\prime $$ ′ -quinolizines] and spiro[indoline-3,4 $$^\prime $$ ′ -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles