6276-48-8

Usage

Uses

Used in Pharmaceutical Industry:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is used as a precursor in the preparation of benzodiazepine pharmacophores, including s-triazine derivatives, which exhibit medicinal properties and potential therapeutic applications.
Used in the Development of Filbanserin:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is an impurity in Filbanserin, a drug that acts as an agonist of the serotonin-5HT1A receptor and an antagonist of the 5-HT2A receptor. It is utilized in the treatment of hypoactive sexual desire disorder in females.
Used in Neurotransmitter Receptor Research:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is also used in the study of its binding affinity to dopamine receptors, with Ki values ranging from 4-24 nM, which can provide insights into its potential role in modulating neurotransmitter activity and related disorders.

InChI:InChI=1/C10H10N2O/c1-7-6-10(13)12-9-5-3-2-4-8(9)11-7/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 95-54-5 1,2-diamino-benzene 
• 71-43-2 benzene 
• 90915-86-9 N-(2-nitrophenyl)-3-oxobutanamide 
• 141-97-9 ethyl acetoacetate 
• 127782-85-8 4-[2-[(E)-2-Amino-phenylimino]-prop-(E)-ylidene]-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 137-07-5 2-amino-benzenethiol 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 75-36-5 acetyl chloride 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 3967-01-9 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one 
• 80948-05-6 4a-methyl-2,3-diphenyl-4a,6,7,11b-tetrahydro-1H,5H-1,3-oxazino<3,2-a>-1,5-benzodiazepin-1,6-dion 
• 122773-86-8 acetoacetic acid N-(2-acetamidophenyl)amide 
• 115847-05-7 4-[(E)-2-(3-Nitro-phenyl)-vinyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 83773-11-9 1H-3-p-nitrobenzylidene-2,3-dihydro-4-methyl-1,5-benzodiazepin-2-one 
• 115847-04-6 4-(p-nitrostyryl)-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 127535-63-1 3a-Methyl-1-phenyl-3a,4-dihydro-6H-3-oxa-2,6,10b-triaza-benzo[e]azulen-5-one 
• 83773-14-2 3-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 106366-68-1 3a-Methyl-5-oxo-1,3-diphenyl-3a,4,5,6-tetrahydro-3H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine 
• 52099-72-6 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one 
• 167871-11-6 4-Methyl-3-[1-p-tolyl-meth-(E)-ylidene]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-09-2 3-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-08-1 3-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-07-0 4-Methyl-3-[1-phenyl-meth-(E)-ylidene]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 

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.

Synthesis of highly regioselective bifunctional tricyclic tetrazole-1 H -benzo[ b ][1,4]diazepins

A new approach for the synthesis of arrays of bifunctional tricyclic tetrazole-1H-benzo[b][1,4]diazepines has been investigated. It includes a sequential two-step isocyanide-based condensation reaction of diamines or 2-nitroanilines, ethyl 3-oxobutanoate or 2,2,6-trimethyl-4H-1,3-dioxin-4-one, isocyanides and trimethylsilyl azide in good yields. Georg Thieme Verlag Stuttgart · New York.

Novel syntheses of tetrahydrobenzodiazepines and dihydropyrazines via isocyanide-based multicomponent reactions of diamines

In this work, two novel isocyanide-based mul multicomponent reactions of 1,2-diamine compounds with diketene have been developed as efficient strategies for the synthesis of 2,3,4,5-tetrahydro-lH-benzo[b][l,4]diazepine2-carboxamidcs with regiochemical control and 1,6-dihydropyrazinc-2,3-dicarbonitrilcs in good to excellent yields at ambient temperature.

A facile and efficient synthesis of arylsulfonamido-substituted 1,5-benzodiazepines and N-[2-(3-benzoylthioureido)aryl]-3-oxobutanamide derivatives

A facile and efficient synthesis of 1,5-benzodiazepines with an arylsulfonamido substituent at C(3) is described. 1,5-Benzodiazepine, derived from the condensation of benzene-1,2-diamine and diketene, reacts with an arylsulfonyl isocyanate via an enamine intermediate to produce the title compounds of potential synthetic and pharmacological interest in good yields (Scheme 1). In addition, reaction of benzene-1,2-diamine and diketene in the presence of benzoyl isothiocyanate leads to N-[2-(3-benzoylthioureido)aryl]-3- oxobutanamide derivatives (Scheme 2). This reaction proceeds via an imine intermediate and ring opening of diazepine. The structures were corroborated spectroscopically (IR, 1Hand 13C-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 3).

Neat reaction technology for the synthesis of novel 1,5-benzodiazepines

A convenient, solvent-free, green approach is described for the synthesis of novel 1,5-benzodiazepines by the reaction of ethylacetoacetate, aldehyde, and o-phenylenediamine without any catalyst at pH 7. Copyright Taylor & Francis Group, LLC.

On the magic of microwave-assisted organic synthesis - 1,5-benzodiazepin-2- one from o-phenylenediamine and ethyl acetoacetate

Microwave-assisted synthesis of 4-methyl-2,3-dihydro-H-1,5-benzodiazepin-2- one by the condensation of 1,2-phenylenediamine and ethyl acetoacetate was examined. The yields were compared with those by classical heating under various conditions. The yield is mainly determined by the temperature of the reaction mixtures, and little affected by the difference in the heating methods. Nonthermal effects in microwave heating have not been observed. Copyright

A facile synthesis of substituted benzodiazepines using solid support

An easy and convenient synthetic procedure for the preparation of benzodiazepines by coupling microwaves with the solvent technique have been elaborated.

Rate enhancement of organic reactions by microwaves at atmospheric pressure

Several different reactions have been studied to determine whether they occur more rapidly than conventionally heated reactions at atmospheric pressure. Small rate enhancements have been observed for some reactions carried out under microwave reflux in a modified domestic microwave oven. The Knoevenagel reaction of acetophenone with ethyl cyanoacetate was shown to have a rate enhancement of 2.5 times. However this reaction showed no rate increase over conventional heating, at the same temperature, in a variable-frequency microwave oven. It is therefore probable that the small rate enhancements observed in these experiments, using microwave heating, were due to hot spots or superheating of the solvent rather than to nonthermal effects.

Pesticidal Activities of Some 3-Aryl-4-methylpyrazolobenzodiazepines and 4-Aryl-2-imino-5-methyl-1,3-thiazinobenzodiazepines

A number of 3-aryl-4-methylpyrazolobenzodiazepines and 4-aryl-2-amino-5-methyl-1,3-thiazinobenzodiazepines have been synthesized from 3-(arylmethylene)-4-methyl-1,5-benzodiazepin-2-one by cyclocondensation with hydrazine hydrate and thiourea in basic medium, respectively.All of the compounds were evaluated for their insecticidal and fungistatic activities, and the results are compared with the standard insecticide Propoxure and the standard fungicide Maneb.Some structure-activity relationships are discussed on the basis of screening data. - Keywords: Pyrazolobenzodiazepines; thiazinobenzodiazepines; insecticidal and fungistatic activities