That's a good complement to these writeups by the late PsychoChemist:
Nordiazepam
(
https://www.thevespiary.org/rhodium/Rhodium/chemistry/nordiazepam.html)
Nitrazepam
(
https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrazepam.html)
Here are the above listed articles:
NitrazepamQuinazolines and 1,4-Benzodiazepines. X. Nitro-Substituted 5-Phenyl-1,4-benzodiazepine DerivativesL. H. Sternbach, R. Ian Fryer, O. Keller, W. Metlesics, G. Sach, N. SteigerJ. Med. Chem. 6, 261-265 (1963)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/benzodiazepines-10.nitrazepam.pdf)
AbstractThe general synthesis of nitro-substituted 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones from aminonitrobenzophenones and the specific synthesis of 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-ones by direct nitration of the corresponding unsubstituted benzodiaxepinones is described. The position of the nitro group was proved by its replacement by chlorine via a Sandmeyer reaction of the amine obtained by reduction. Alkylation of some of the benzodiazepinones gave the corresponding 1-alkyl derivatives. Mild acid hydrolysis of nitrobenzodiazepinones and 1-alkyl-nitrobenzodiazepinones led to several previously undescribed aminonitrobenzophenones. 2-Amino-5-nitrobenzophenone was converted aia the a-oxime into the corresponding 2-chloromethyl-6-nitro-4-phenylquinazoline 3-oxide and this compound when treated with nucleophilic reagents gave, by a ring expansion, 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide. The pharmacological properties of three nitrobenzodiazepine derivatives are reported. These compounds showed a low toxicity combined with sedative, muscle relaxant and anticonvulsant properties.
NordiazepamQuinazolines and 1,4-Benzodiazepines. IV. Transformations of 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 4-OxideL. H. Sternbach, E. ReederJ. Org. Chem. 26, 4936-4941 (1961)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/benzodiazepines-04.nordiazepam.pdf)
Abstract7-Chloro-2-methylamino-5-phenvl-3H-1,4-benzodiazepine 4-oxide (I) and its acetyl derivative (II) can be hydrolyzed to 7-chloro-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one 4-oxide (III). Other methods are described for the synthesis of this compound and its conversion into pharmacologically active beneodiazepinones.
1,3-Dihydro-2H-1,4-benzodiazepine-2-ones and Their 4-OxidesS. C. Bell, T. S. Sulkowski, C. Gochman, S. J. ChildressJ. Org. Chem. 27, 562-566 (1962)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/benzodiazepine-2-ones.nordiazepam.pdf)
AbstractAlcoholic sodium hydroxide converts 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide (I) into 7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-one 4-oxide (II). 7-Chloro-5-phenyl-1,3-dihydro-2H-1,4benzodiazepine-2-one (III) was prepared by reduction of II and by several alternate routes. A number of analogs were made.