A Novel Entry to Spirofurooxindoles Involving Tandem Dearomatization of Furan Ring and Intramolecular Friedel- Crafts Reaction

A copper sulfate pentahydrate‐catalyzed intramolecular Friedel–Crafts reaction using an oxocarbenium species derived from a furan ring as the alkylating agent was developed for the first time. By using this protocol, spirofurooxindoles 9 with multi‐reactive sites were synthesized simply and concisel...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-08, Vol.353 (11-12), p.1961-1965
Main Authors: Yin, Biao-Lin, Lai, Jin-Qiang, Zhang, Ze-Ren, Jiang, Huan-Feng
Format: Article
Language:English
Subjects:
Alkylation
BONDING
Catalysis
Chemistry
Copper
COPPER SULFATE
dearomatization
Exact sciences and technology
FABRICATION
Friedel-Crafts reaction
Furans
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
HYDROGENATION
Organic chemistry
Preparations and properties
selective hydrogenation
spirofurooxindoles
SULFATES
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:A copper sulfate pentahydrate‐catalyzed intramolecular Friedel–Crafts reaction using an oxocarbenium species derived from a furan ring as the alkylating agent was developed for the first time. By using this protocol, spirofurooxindoles 9 with multi‐reactive sites were synthesized simply and concisely. In addition, selective hydrogenation of the endo‐cyclic double bond and full hydrogenation of the endo and exo‐cyclic double bonds of spirofurooxindoles 9 provided spirofurooxindoles 11 and 12, respectively.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100034