Syntheses of Benzodiazepine Derivatives

Autor: Motoki, Shinichi, Urakawa, Chikahiro, Kano, Akio, Fushimi, Yukio, Hirano, T\={o}ru, Murata, Katsumi
Zdroj: Bulletin of the Chemical Society of Japan; March 1970, Vol. 43 Issue: 3 p809-813, 5p
Abstrakt: This communication deals with the syntheses of the aza-analogues of benzoheptafulvene. Acetylacetone or benzoylacetone reacted with benzophenone chloride in the presence of sodium ethoxide to form 3-(a-phenylbenzylidene)pentane-2,4-dione (XIVa) or 1-phenyl-2-(a-phenylbenzylidene) butane-1,3-dione (XIVc) respectively. Treatment of o-phenylenediamine with XIVa in acetic acid - ethanol resulted in forming 2,4-dimethyl-3-(a-phenylbenzylidene)-3H-benzo[b]-1,5-diazepine (XVa) which has a 3,6-diaza-4,5-benzoheptafulvene ring skeleton. Similarly, substituted o-phenylenediamines reacted with XIVa to give 7-substituted 2,4-dimethyl-3-(a-phenylbenzylidene)-3H-benzo[b]-1,5-diazepines (XVb)—(XVd). Reaction of XIVa with hydrazine gave only the monohydrazone of XlVa. The ketene dimer reacted with o-phenylenediamines to give 4-methyl-2,3-dihydro-2-oxo-1H-benzo[b]-1,5-diazepines (Xa)—(Xc). However, the condensation of Xa with aldehyde gave an undesirable product.
Databáze: Supplemental Index