Unexpected Opening of the Benzodiazepine Ring During Acetylation

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.

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