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An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations.
MedLine Citation:
PMID:  22543858     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.
Authors:
Takuya Yokosaka; Tetsuhiro Nemoto; Yasumasa Hamada
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-4-27
Journal Detail:
Title:  Chemical communications (Cambridge, England)     Volume:  -     ISSN:  1364-548X     ISO Abbreviation:  -     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-4-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9610838     Medline TA:  Chem Commun (Camb)     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. hamada@p.chiba-u.ac.jp.
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