The Rearrangement of 2-Amino-5-phenyl-3H-1,4-benzodiazepine 4-Oxides with Acetic Anhydride

Abstract

A mixture melting point with authentic material prepared as described19 showed m.p. 103-105°. The infrared spectra of the two compounds were superimposable.Decarboxylation of II to Give I.-A mixture of 1 g. of II and 1 g. of copper powder in 25 ml. of quinoline was heated under reflux for 3 hr. The mixture was filtered, 50 ml. of chloroform was added, and the organic phase was washed in turn with N hydrochloric acid and water. The organic phase was dried and

General route for the facile synthesis of pyrimidin-2-one-4-thione derivatives via the annulation of cyclic o-aminonitriles using carbonyl sulfide

“…The solvent was removed in vacuo and the residual data): C, 43.19; H, 4.37;N,21.59. Found: C,42.96;H,4.36;N,21.50. 4-Amino-9-(/S-D-ribofuranosyl)pyrrolo [2,3-d:5,4-d']dipyrimidin-5,7-dione (5). 4-Amino-9-(/S-D-ribofuranosy 1)pyrrolo-[2,3-d:5,4-d/]-5-thioxodipyrimidin-7-one (3; 150 mg, 0.41 mmol) was dissolved in aqueous ammonium hydroxide (10 mL of 28.7% solution).…”

Über 3H‐1,4‐Benzodiazepine mit semicyclischer Hydroxyamidin‐Struktur und deren oxidoreduktive 1,3‐Umlagerung zu 2‐Alkylamino‐3‐acyloxy‐3H‐1,4‐benzodiazepinen

“…C 60, 6 H 4,80 C19,9 N 15,7 Gef. C 60,5 H 4,77 CI 10,O N 15,6. -N-(7-chlor-5-phenyl-3H-II 4-benzodiazepin-2-y[) 5 H 5,83 N 11,2 Gef.…”

“…In der gleichen Weise wurde aus lb und Acetanhydrid 5b gebildet. Die Struktur des 3-Acyloxy-Derivates 5a konnten wir spektroskopisch und durch eine authentische Syntheseh e r iiber eine ebenfalls oxidoreduktive Umlagerung des Nitrons Chlordiuzepoxid (6) hangigen Synthese konnten wir 10 durch einstundiges Erhitzen des gemischten Kohlensaureesters 11 im Hochvakuum herstellen.…”

Studies on Benzodiazepinooxazoles. III. Reactions and Rearrangements of Benzo [6, 7]-1, 4-diazepino-[5, 4-<I>b</I>] oxazole Derivatives

“…Bromo -2,3,5, 6, 7,11 b-hexahydro -5-methylene -7-methyl -11b-phenylbenzo [6,7] -1,4-diazepino[5,[4][5][6][7][8][9][10]]oxazol-6-one (Vb)-The reaction of 10-bromo-2,3,5,6,7,11b-hexahydro-7-methyl-11b-phenylbenzo[6,7]-1,4-diazepino[5,4-b]-oxazol-6-one (IIIb) (3.73 g) and NaH (0.48 g) in 40 ml of DMF afforded Vb (1.54 g) J=1.2 Hz, >C=CH2) 4.22 (2H, multiplet, -CH2 -O-), 7.3 (center, 8H, multiplet, aromatic protons). Anal.…”