Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-07, Vol.80 (14), p.7226-7234
Main Authors: Gazzola, Silvia, Beccalli, Egle M, Borelli, Tea, Castellano, Carlo, Chiacchio, Maria Assunta, Diamante, Daria, Broggini, Gianluigi
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Copper - chemistry
Halogenation
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Urea - chemistry
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Summary:A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01227