Abstract
Reaction of 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines 1 either with acetyl chloride in dry CH2Cl2 in the presence of pyridine, or with acetic anhydride in the presence or absence of base afforded, after unexpected opening of the benzodiazepine ring, N-butenylidene-amino-phenylacetamides 3 in excellent yields instead of the expected ring tautomers 2.
Keywords: 2,3-dihydro-1H-1, 5-benzodiazepines, acetylation, 2-N-butenylidene-amino-phenylacetamides, benzodiazepine ring opening, ring-chain tautomerism
Letters in Organic Chemistry
Title: Unexpected Opening of the Benzodiazepine Ring During Acetylation
Volume: 5 Issue: 1
Author(s): Constantinos A. Tsoleridis, Constantinos Neochoritis, Minodora Pozarentzi and Julia Stephanidou-Stephanatou
Affiliation:
Keywords: 2,3-dihydro-1H-1, 5-benzodiazepines, acetylation, 2-N-butenylidene-amino-phenylacetamides, benzodiazepine ring opening, ring-chain tautomerism
Abstract: Reaction of 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines 1 either with acetyl chloride in dry CH2Cl2 in the presence of pyridine, or with acetic anhydride in the presence or absence of base afforded, after unexpected opening of the benzodiazepine ring, N-butenylidene-amino-phenylacetamides 3 in excellent yields instead of the expected ring tautomers 2.
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Cite this article as:
Tsoleridis A. Constantinos, Neochoritis Constantinos, Pozarentzi Minodora and Stephanidou-Stephanatou Julia, Unexpected Opening of the Benzodiazepine Ring During Acetylation, Letters in Organic Chemistry 2008; 5 (1) . https://dx.doi.org/10.2174/157017808783330225
DOI https://dx.doi.org/10.2174/157017808783330225 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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