Open AccessFormation of Benzodiazepines and Pyrazinylquinoxalines from Aromatic and Heteroaromatic Ketones via Deoximation
Author(s) -
Jae Min Song,
Song Mi Bae,
E.J. Lee,
Jong Hyun Cho,
DaiIl Jung
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22639
Subject(s) - chemistry , acetophenone , ketone , oxime , benzophenone , acetone , diamine , organic chemistry , quinoxaline , medicinal chemistry , pyridine , reagent , catalysis
The report stated that the treatment of o-phenylenediamine with acetone dicarboxylic acid, acetoneand acetophenone afforded 2,4,4-trimethyl-3H-5-hydro-1,5-benzodiazepine. However, direct reactionsof 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 thatdichloroamine-T can be an efficient reagent for the conversion of oximes into the corresponding carbonylcompounds. As a part of a research program related to the synthetic study of pharmacologicallyinteresting benzodiazepine compounds, herein the synthesis of 1H-1,5-benzodiazepine derivativesfrom heteroaromatic ketones and acetone equivalents obtained using dichloroamine-T. On the otherhand, 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, quinoxalinederivatives as yellow crystalline solids were isolated in high yields