16442-59-4

Upstream product

• 122773-88-0 5-acetyl-4-phenyl-1,5-dihydro-1H-1,5-benzodiazepin-2-one 
• 16439-95-5 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 70-11-1 α-bromoacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 75-36-5 acetyl chloride 

Downstream Products

• 122773-90-4 1,5-diacetyl-4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one 
• 105931-88-2 1-benzyl-4-phenyl-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one 

Relevant academic research and scientific papers

Experimental and theoretical investigation of substituent effects in a two-pathway reaction of tetrahydro-1,5-benzodiazepine-2-thiones with 4-substituted 2-bromoacetophenones

The interaction of 5-acetyl(or formyl)-3-R1(CH3, H)-4-R2(CH3, Ph, H)-1,3,4,5-tetrahydro-2H-1,5- benzodiazepine-2-thiones with 2-bromo-4′-X(CH3, OCH 3, Br, H)-acetophenones leads to a mixture of products: 5,6-dihydro-4H-[1,3]thiazolo[3,2-a][1,5]benzodiazepinium salts and S-[2-oxo-2-(4-X-phenyl)ethyl] 3-(1H-benzimidazol-1-yl)propane(or butane-)thioate hydrobromides. The course of the concurrent reactions depends on the presence of substituents of the starting thiones and on the nature of the 4-substituent of the bromoacetophenones. Semiempirical Austin method 1 (AM1) and density functional theory (DFT) B3LYP computational studies for the interpretation of two concurrent reaction pathways are presented.

Asymmetric Hydrogenation of Cyclic Imines and Enamines: Access to 1,5-Benzodiazepine Pharmacophores

A new strategy towards the pharmacologically relevant class of dihydro-1,5-benzodiazepines was developed by applying a rhodium-catalyzed asymmetric hydrogenation. The approach represents an efficient protocol providing access to the optically active products in excellent yields (up to 99%) and with high enantioselectivities (up to 92% ee). The versatility of the methodology was demonstrated by a broad substrate scope including alkyl, aryl, and heteroaryl substituents as well as halides. Furthermore, investigations regarding the reaction mechanism were performed and unraveled a preferred reaction of the tautomeric enamine in the rhodium-catalyzed asymmetric hydrogenation.

TRANSFORMATION OF DIHYDRO-1,5-BENZODIAZEPIN-2-ONES UNDER THE INFLUENCE OF ACETIC ANHYDRIDE

The acylation of 4-R-2,3-dihydro-1H-1,5-benzodiazepin-2-ones leads to isomerization or opening of the heteroring with subsequent acylation. 1-Acyl-2,3-dihydro-1,5-benzodiazepin-2-ones are not formed.