Unexpected Opening of the Benzodiazepine Ring During Acetylation

Constantinos   A.   Tsoleridis; Constantinos      Neochoritis; Minodora      Pozarentzi; Julia      Stephanidou-Stephanatou

doi:10.2174/157017808783330225

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

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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

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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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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