Synthesis and biological activity of N-substituted 2,3,4,5-tetrahydro-1H-1,5-Benzodiazepin-2-ones

Synthesis of novel annelated systems based on the interaction and reactivity estimation of amino‐1,5‐benzodiazepin‐2‐ones with dimethyl‐2‐oxoglutaconate

“…4,5‐Dimethyl‐9‐nitroderivative 8g was prepared by reductive alkylation of dihydronitroderivative 10 with sodium borohydride and formic acid. Compound 9 was synthesized by nitration of 5‐acetyl‐3‐methyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one [13]. The starting aminobenzodiazepinones carrying various alkyl groups at the N 1 and N 5 atoms of the diazepine heterocycle ring were chosen for their acute solubility in organic solvents.…”

“…A solution of 2.2 g (10.0 mmol) of 5‐acetyl‐3‐methyl‐1,3,4,5‐tetrahydro‐2 H ‐1,5‐benzodiazepin‐2‐one [13] in 30 mL of conc. sulfuric acid, and a solution of 2.2 g (20.0 mmol) of potassium nitrate in 25 mL of conc.…”

A convenient synthesis of novel substituted imidazo[1,2-a][1,5]benzodiazepine derivatives

“…The synthesis of N 1 -substituted derivatives 2a-f was achieved starting from the known 5-acetyl-1,5-benzodiazepinones 1a-c 12 Method A. To a stirred suspension of a suitable acetylbenzodiazepinone derivative 1a-c (4.5 mmol), finely powdered potassium hydroxide (1.26 g, 22.5 mmol) in dry acetone (40 ml), a precooled solution of chloroacetone (0.73 ml, 9.0 mmol) in dry acetone (10 ml) or solution of 2-bromoacetophenone (1.79 g, 9.0 mmol) in dry acetone (60 ml) was added dropwise (15 min.)…”

Novel synthesis of quinazolino[3,2-a][1,5]benzodiazepines: an experimental and computational study

“…Microanalyses were performed with Thermo Scientific TM Flash 2000 CHNS/O analyser. The synthesis and NMR spectral data of the starting 5-acetyl-(1a), 43 5-formyl-(1b), 44 5-benzoyl-(1c), 19 5-methyl-(1e) 45 and 5-benzyl-(1f) 46 benzodiazepinones were published previously; the newly synthesized 5-ethoxycarbonyl compound 1d is described here. General procedure for the synthesis of 5-R-7-methyl-6,7-dihydroquinazolino[3,2-a]-[1,5]benzodiazepin-13(5H)-ones (5a-f, 8 and 9).…”