Direct Reductive Cyclocondensation of the Nitro Group with the Amido Group: Key Role of the Iminophosphorane Intermediate in the Synthesis of 1,4-Dibenzodiazepine Derivatives

A class of dialkylamino-substituted dibenzodiazepines and their hetero analogues was synthesized by the intramolecular aza-Wittig condensation of the amido group with iminophosphoranes. The one-pot, two-step procedure includes reductive synthesis of the intermediate iminophosphoranes from the corres...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-02, Vol.84 (4), p.2277-2286
Main Authors: Tryniszewski, Michał, Bujok, Robert, Cmoch, Piotr, Gańczarczyk, Roman, Kulszewicz-Bajer, Irena, Wróbel, Zbigniew
Format: Article
Language:English
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Summary:A class of dialkylamino-substituted dibenzodiazepines and their hetero analogues was synthesized by the intramolecular aza-Wittig condensation of the amido group with iminophosphoranes. The one-pot, two-step procedure includes reductive synthesis of the intermediate iminophosphoranes from the corresponding nitroamides and tributylphosphine.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02682