16442-58-3

Upstream product

• 16439-95-5 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 95-54-5 1,2-diamino-benzene 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 

Downstream Products

• 119483-55-5 4-Oxo-2-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbaldehyde 
• 1201652-42-7 ethyl 4-oxo-2-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carboxylate 
• 488737-01-5 4-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-thione 

Relevant academic research and scientific papers

Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands

The catalytic hydrogenation of benzodiazepinones using metal complexes with phosphite and phosphoramidite ligands was carried out for the first time. The mixed-ligand catalytic systems containing a chiral phosphoramidite or phosphite in combination with an achiral phosphine were shown to exhibit a higher enantioselectivity compared to catalysts containing homocombinations of chiral ligands.

Synthesis of new chiral amidophosphite ligands and their application in hydrogenation of benzodiazepinones and enamides

New chiral amidophosphites were synthesized and tested in the Ir-catalyzed hydrogenation of 4-substituted 1,3-dihydro-2H-1,5-benzodiazepin-2-ones and Rh-catalyzed hydrogenation of dehydro amino acid derivatives. The triphenylphosphine additive can considerably increase the enantioselectivity of both processes.

Asymmetric Ir-catalyzed hydrogenation of 1,3-dihydro-2H-1,5-benzodiazepin-2-ones using phosphoramidites

A series of phosphoramidite ligands was tested in the asymmetric hydrogenation of 4-arylsubstituted 1,3-dihydro-2H-benzodiazepine-2-ones and up to 52% ee was achieved. The effects of various factors (solvents, hydrogen pressure, and addition of phosphine

Direct and Enantioselective Synthesis of N?H-Free 1,5-Benzodiazepin-2-ones by an N-Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction

An NHC-catalyzed formal [3+4] annulation of α,β-unsaturated acylazoliums with protecting-group-free aryl 1,2-diamines was developed for a direct and highly enantioselective synthesis of 4-aryl N?H-free 1,5-benzodiazepin-2-ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N-functionalization to afford diverse N-substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.

Asymmetric Hydrogenation of Cyclic Imines of Benzoazepines and Benzodiazepines with Chiral, Cationic Ruthenium–Diamine Catalysts

A method for the highly enantioselective hydrogenation of diverse seven-membered N-containing heterocycles, including 2,4-diaryl-3H-benzo[b]azepines, racemic 2,2,4-trisubstituted 2,3-dihydrobenzo[b][1,4]diazepines, and 4-substituted 1H-benzo[b][1,4]diazep

COMPOUNDS WHICH HAVE A PROTECTIVE ACTIVITY WITH RESPECT TO THE ACTION OF TOXINS AND OF VIRUSES WITH AN INTRACELLULAR MODE OF ACTION

The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.

Enantioselective synthesis of 4-substituted 4,5-dihydro-1 H-[1,5]benzodiazepin-2(3 H)-ones by the Lewis base-catalyzed hydrosilylation

Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5] benzodiazepin-2(3H)-ones has been accomplished through chiral Lewis base-catalyzed hydrosilylation. The corresponding products were obtained in excellent yields (up to 99%) and enantioselect

Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds

Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3-5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.

Efficient syntheses of β-amino-N-acylbenzotriazoles and cinnamides through regioselective 1,4- or 1,2-addition of amines to N- cinnamoylbenzotriazoles

Amines react with N-cinnamoylbenzotriazoles to afford either β-amino-N-acylbenzotriazoles or cinnamides depending on the structure of the amines. Aromatic amines react with N-cinnamoylbenzotriazoles via 1,4-addition to give β-amino-N-acyl-benzotriazoles in good yields. For o-phenylenediamine, the 1,4-addition products were further acylated to provide a facile route to substituted 1,3,4,5-tetrahydro-1,5-benzodiazepine-2-ones. Aliphatic amines, however, react exclusively through the 1,2-addition pathway to produce cinnamides in good yields. Georg Thieme Verlag Stuttgart.