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

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 -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 AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s11030-013-9459-5) contains supplementary material, which is available to authorized users.

Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies

“…However no dr ratio was mentioned (scheme 20B). 77 Shi and co-workers have reported a three-component condensation of a pyridine, an acetylenedicarboxylates, and an N-substituted isatylidene to afford the spiro[indoline-3,3- piperidin]-2-one skeleton 96 under mild reaction conditions (Scheme 20C). 78 A variety of 1,9adihydrospiro[indoline-3,2-quinolizin]-2-one derivatives 96 were obtained in moderate to excellent yields (53-99%) and with good to excellent dr values (up to 99:1).…”

One‐pot Two‐Step Cycloaddition Reaction for Convenient Synthesis of Polycyclic Spirooxindole‐fused [1,3]Oxazines

“…[28][29][30][31][32][33][34][35][36][37][38][39][40] Recently, we successfully found that spiro[indoline-3,1'-quinolizin]-2-ones, which were generated from the three-component reaction of substituted pyridine, acetylenedicarboxylate and 3-phenacylideneoxindoles, could undergo Diels-Alder reaction with the typical dienophiles such as maleic anhydride and N-phenylmaleimides. [41][42][43] Alternatively, spiro[3H-indole-3,2'-[2H,9aH-pyrido [2,1-b] [1,3]oxazine], which were formed from three-component reaction of the substituted pyridines, electron-deficient alkynes and isatins, also underwent Diels-Alder reaction with 3-phenacylideneoxindoles (eq. 1 in Scheme 1).…”