The report stated that the treatment of o-phenylenediamine with acetone dicarboxylic acid, acetone
and acetophenone afforded 2,4,4-trimethyl-3H-5-hydro-1,5-benzodiazepine. However, direct reactions
of o-phenylenediamine with oximes (acetone oxime, acetophenone oxime, and benzophenone oxime)
as ketone equivalents did not occur. In the course of present investigations, it is found that
dichloroamine-T can be an efficient reagent for the conversion of oximes into the corresponding carbonyl
compounds. As a part of a research program related to the synthetic study of pharmacologically
interesting benzodiazepine compounds, herein the synthesis of 1H-1,5-benzodiazepine derivatives
from heteroaromatic ketones and acetone equivalents obtained using dichloroamine-T. On the other
hand, when diamine (1,2-phenylene diamine or 1,2-naphthalene diamine) with heterocyclic ketone
(acetyl pyridine or acetyl pyrazines) in the presenece of conc. HCl and SiO2 was refluxed, quinoxaline
derivatives as yellow crystalline solids were isolated in high yields
Rhodium-Catalyzed ortho-Alkenylation of Phenols Directed by Acetone Oxime Ether
