A simple route to tetrahydro-1,4-benzodiazepin-3-ones bearing diverse N1, N4, and C10 functionalization

[Display omitted] We describe an efficient synthesis of enantiopure tetrahydro-1,4-benzodiazepine-3-ones derived from l-alanine. Diverse substitution at N1, N4, and C10 can be achieved by coupling various N-alkyl derivatives of l-alanine and N-allyl-(2-fluoro-5-nitro)benzylamine. Cyclization of this...

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Bibliographic Details
Published in:Tetrahedron letters 2005-05, Vol.46 (21), p.3633-3635
Main Authors: Clement, Ella C., Carlier, Paul R.
Format: Article
Language:English
Subjects:
Benzodiazepine
Nucleophilic aromatic substitution
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Summary:[Display omitted] We describe an efficient synthesis of enantiopure tetrahydro-1,4-benzodiazepine-3-ones derived from l-alanine. Diverse substitution at N1, N4, and C10 can be achieved by coupling various N-alkyl derivatives of l-alanine and N-allyl-(2-fluoro-5-nitro)benzylamine. Cyclization of this intermediate proceeds in high yield and without racemization, providing diversity at N1. The NO 2 group was easily transformed into other functional groups or removed, providing diversity at C10. Finally, oxidative deallylation allows diverse substitution to be installed at N4.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.03.171