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Synfacts 2008(12): 1260-1260  
DOI: 10.1055/s-0028-1087328
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Synthesis of 1,5-Benzo-
diazepines

Contributor(s): Victor Snieckus, Johnathan Board
B. Willy, T. Dallos, F. Rominger, J. Schönhaber, T. J. J. Müller*
Heinrich-Heine-Universität Düsseldorf, Ruprecht-Karls-Universität Heidelberg, Germany and Babes-Bolyai University Cluj-Napoca, Romania
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

Reported is the one-pot synthesis of substituted benzodiazepines from acyl chlorides, alkynes and ortho-aminoanilines. Sonogashira-type cross-coupling leads to the formation of the intermediate alkynone, which then undergoes reaction with the aminoaniline to give the di­azepine. Conventional oil-bath heating appeared to give better yields than microwave conditions, but the former required longer reaction times. The availability of substituted phenylenediamines is, of course, crucial to the achievable substitution patterns of the product benzodiazepines.