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Synthesis 2020; 52(20): 3086-3094
DOI: 10.1055/s-0040-1707347
DOI: 10.1055/s-0040-1707347
paper
Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones
Further Information
Publication History
Received: 26 February 2020
Accepted after revision: 28 May 2020
Publication Date:
21 July 2020 (online)
Abstract
Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707898.
- Supporting Information
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