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Efficient Synthesis of Spiro[furan‐3,3′‐indoline] Derivatives via Reactions of Pyridinium Salts with Isatinylidene Acetoacetates
Author(s) -
Liu Zhenming,
Fang Jun,
Yan Chaoguo
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300407
Subject(s) - chemistry , indoline , pyridinium , triethylamine , furan , intramolecular force , ylide , organic chemistry , bromide , domino , medicinal chemistry , catalysis
An efficient synthetic procedure for the functionalized spiro[furan‐3,3′‐indoline] derivatives was successfully developed by domino reactions of N ‐phenacylpyridinium bromides or N ‐ethoxycarbonylmethylenepyridinium bromide with isatinylidene acetoacetate in the presence of triethylamine in ethanol at room temperature. The mechanism included sequential Michael addition of the in situ generated pyridinium ylide and intramolecular substitution of enolate.