Document Detail


Iron(III) Chloride/Diorganyl Diselenides: A Tool for Intramolecular Cyclization of Alkynone O-Methyloximes.
MedLine Citation:
PMID:  23351114     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
This report describes the synthesis of 4-organoselenyl-isoxazoles via FeCl3/RSeSeR-mediated intramolecular cyclization of alkynone O-methyloximes. The optimized conditions allowed the cyclization to proceed at room temperature, under ambient atmosphere and the reaction requires a short time to be completed. The reaction conditions tolerated neutral, electron-donating and electron-withdrawing groups present in both substrates, alkynone O-methyloximes and diorganyl diselenides. Treatment of 4-organoselenyl-isoxazoles with n-butyl lithium, followed by trapping with electrophiles, furnished the functionalized isoxazoles in good yields. The obtained products also proved to be suitable substrates for the preparation of 4-bromo-isoxazoles via Br/Se exchange reaction.
Authors:
Adriane Sperança; Benhur Godoi; Gilson Zeni
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-27
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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