Synfacts 2009(2): 0133-0133  
DOI: 10.1055/s-0028-1087578
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Three-Component Synthesis of Tetrahydro-1H-1,5-benzodiazepines

Contributor(s): Victor Snieckus, Dmitry N. Korolev
A. Shaabani*, A. Maleki, H. Mofakham
Shalid Beheshti University, Tehran, Iran
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Publikationsverlauf

Publikationsdatum:
22. Januar 2009 (online)

Significance

Reported is a simple and convenient one-pot three-component synthesis of ­tetrahydro-1H-1,5-benzodiazepine-2-carbox­amides from o-phenylenediamines, ketones and isocyanides. First performed is the in situ generation of diimines which undergo intramolecular cyclization to give dihydro-1H-1,5-benzodiazepines (not shown) which are subjected to reaction with isocyanides resulting in the formation of the target diazepines in good to excellent yields. The protocol uses simple and mild conditions allowing the synthesis of combinatorial libraries with various substitution patterns.