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Nitrogen‐ and Phosphorus‐Containing Lewis Base Catalyzed [4+2] and [3+2] Annulation Reactions of Isatins with But‐3‐yn‐2‐one
Author(s) -
Lian Zhong,
Shi Min
Publication year - 2012
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.201101338
Subject(s) - indoline , chemistry , annulation , catalysis , lewis acids and bases , phosphorus , nitrogen , base (topology) , substrate (aquarium) , organic chemistry , medicinal chemistry , mathematical analysis , oceanography , mathematics , geology
Nitrogen‐ and phosphorus‐containing Lewis base catalyzed [4+2] and [3+2] annulations of isatins with but‐3‐yn‐2‐one proceeded smoothly to give the corresponding spiro[indoline‐3,2′‐pyran]‐2,4′(3′ H )‐diones and spiro[furan‐2,3′‐indoline]‐2′,4(5 H )‐diones in good‐to‐excellent yields under mild conditions. The substrate scope has been carefully examined. Moreover, the additive effect of water has also been investigated in detail along with plausible reaction mechanisms based on previous literature and our own investigations.