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A Three‐Component Reaction for the Synthesis of Diverse, Densely Substituted 2′,3′‐Dihydrospiro[indoline‐3,6′‐[1,3]oxazine]s
Author(s) -
Zhang Jing,
Gao Hong,
Sun Jing,
Yan ChaoGuo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402500
Subject(s) - indoline , chemistry , acetylenedicarboxylate , component (thermodynamics) , dimethyl acetylenedicarboxylate , aryl , organic chemistry , medicinal chemistry , combinatorial chemistry , cycloaddition , catalysis , alkyl , physics , thermodynamics
A simple synthetic protocol has been developed for the efficient synthesis of structurally diverse 3′‐aryl‐2′‐styryl‐2′,3′‐dihydrospiro[indoline‐3,6′‐[1,3]oxazine]‐4′,5′‐dicarboxylate derivatives through readily accessible three‐component reactions of α,β‐unsaturated N ‐arylaldimines, dialkyl acetylenedicarboxylate, and N ‐alkylisatins. When simple N ‐arylaldimines were utilized in the reactions, the corresponding 2′,3′‐diaryl‐2′,3′‐dihydrospiro[indoline‐3,6′‐[1,3]oxazine]s were obtained in good yields. This reaction provides a potential synthetic application of the reactive 1,4‐dipolar intermediates generated from the reaction of aromatic imines with electron‐deficient alkynes.