Design, Synthesis, and Characterization of 1, 3-disubstituted-1,4-benzodiazepine Derivatives.

The 2-amino-4′-flouro-benzophenone ( 1) that was reacted with chloroacetylchloride to afford 2-chloro- N-(2-(4′-fluorobenzoyl) phenyl)acetamide ( 2) was subsequently converted to 1,4-benzodiazepines ( 3) by the modification of the known hexamethylenetetramine based reaction developed by Blazevic and Kajfez. Thus, obtained product ( 3) was reacted with a variety of alkyl halide using KOH in DMF to give 1-substituted-5-(4-fluorophenyl)-1 H-benzo[e][1,4]diazepin-2(3 H)-one ( 4a, 4b). To achieve 1, 3-disubstituted 1, 4-benzodiazepines ( 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, 5p, 5q, 5r, 5s, 5t), 1-substituted-5-(4-fluorophenyl)-1 H-benzo[e][1,4]diazepin-2(3 H)-one ( 4a, 4b) was treated with various aromatic aldehydes in the presence of KOH in toluene. [ABSTRACT FROM AUTHOR]