Leo Henryk Sternbach

The reaction of epoxides with 1,4-benzodiazepines, mechanism and structural assignments

Abstract The reaction of epoxides with the imine moiety of 1,3-dihydro-2 H -1,4-benzodiazepin-2-ones yields oxazolo[3.2-d][1.4]-benzodiazepin-6-(7 H )-ones. A SN-2 initiated two-step mechanism is proposed. The reaction of propylene oxide with 7-chloro-1,3-dihydro-5-phenyl-2 H -1,4-benzodiazepin-2-one affords a mixture of epimers which are resolved and to which structures are assigned.

Chinazoline und 1,4-Benzodiazepine, 35. Mitt.: Darstellung und Umlagerungsreaktionen eines 3,1,4-Benzoxadiazepines

Das 7-Chlor-2-methylamino-5-phenyl-3,1,4-benzoxadiazepin wurde dargestellt und die Umlagerungsreaktionen dieser Verbindung wurden untersucht. Je nach den Reaktionsbedingungen wurden Indazol-, Benzoxazin- oder Chinazolinderivate erhalten.

Quinazolines and 1,4-benzodiazepines. Part XXXII. The acetic anhydride rearrangement of 1,4-benzodiazepinones to isoindoles

1,3-Dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones unsubstituted in the 1-position rearrange to 1-acetyliso-indoles in the presence of acetic anhydride and pyridine. The structure of the rearranged products has been established by alternative syntheses, and the mechanism of the rearrangement is discussed.

Anomalous lithium aluminium hydride reduction of aromatic trifluromethyl groups of methyl groups

Benzotrifluorides which are ortho- or para-substituted by an amino- or a hydroxy-function are easily reduced to the corresponding hydrocarbons by lithium aluminium hydride.

Quinazolines and 1,4-benzodiazepines. Part XXXVIII. The reaction of hydrazines with 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide

The reactions of hydrazines with 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide have been investigated. In the case of hydrazine, a benzodiazepine was obtained, and some of its reactions with acetylating agents are discussed. When 1,1-dimethylhydrazine and methylhydrazine were used, quinazoline hydrazones were obtained. A mechanism is suggested.