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Synthesis 2019; 51(10): 2198-2206
DOI: 10.1055/s-0037-1611734
DOI: 10.1055/s-0037-1611734
paper
Synthesis of 3-Amino-1,5-benzodiazepine-2-one Derivatives from Dehydroalanine Derivatives
Further Information
Publication History
Received: 13 December 2018
Accepted after revision: 18 January 2019
Publication Date:
25 March 2019 (online)
Abstract
A convenient method was developed for synthesizing 3-amino-1,5-benzodiazepine-2-one derivatives via a Michael addition reaction of o-phenylenediamine with dehydroalanine HFI or HOBt ester derivatives (HFI = 1,1,1,3,3,3-hexafluoro-2-propyl; HOBt = 1,2,3-benzotriazol-1-ol monohydrate), followed by cyclization. Interestingly, the regio- and diastereoselectivities were confirmed by comparing the HFI and HOBt esters. These simple methods were used to synthesize various N-substituted 3-amino-1,5-benzodiazepine-2-one derivatives in good yields.
Key words
1,5-benzodiazepines - Michael additions - o-phenylenediamine - dehydroalanine - intramolecular cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611734.
- Supporting Information
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