Formal [4 + 2] Annulation of Oxindole-Embedded ortho-Quinone Methides with 1,3-Dicarbonyls: Synthesis of Spiro[Chromen-4,3′-Oxindole] Scaffolds

The oxindole-embedded ortho-quinone methides were employed as reactive intermediates in formal [4 + 2] annulation with 1,3-dicarbonyls, providing an efficient access to spiro­[chromen-4,3′-oxindole] scaffolds via a cascade conjugate addition/ketalization/dehydration process. This protocol featured m...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-04, Vol.84 (7), p.3990-3999
Main Authors: Shen, Yao-Bin, Li, Shuai-Shuai, Liu, Xicheng, Yu, Liping, Sun, Yun-Ming, Liu, Qing, Xiao, Jian
Format: Article
Language:English
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Summary:The oxindole-embedded ortho-quinone methides were employed as reactive intermediates in formal [4 + 2] annulation with 1,3-dicarbonyls, providing an efficient access to spiro­[chromen-4,3′-oxindole] scaffolds via a cascade conjugate addition/ketalization/dehydration process. This protocol featured metal-free conditions, wide substrate scope, and excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03260