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A Novel Entry to Spirofurooxindoles Involving Tandem Dearomatization of Furan Ring and Intramolecular Friedel– Crafts Reaction
Author(s) -
Yin BiaoLin,
Lai JinQiang,
Zhang ZeRen,
Jiang HuanFeng
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100034
Subject(s) - chemistry , intramolecular force , oxocarbenium , friedel–crafts reaction , furan , ring (chemistry) , tandem , double bond , cascade reaction , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , nucleophile , materials science , composite material
Abstract 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.