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

Abstract

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. Graphical Abstract: [Figure not available: see fulltext.] © 2013 The Author(s).