- 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.
- Lyubimov,Ozolin,Davankov
-
p. 1059 - 1061
(2017/10/31)
-
- 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.
- Sokolovskaya,Lyubimov,Davankov
-
p. 1213 - 1216
(2017/12/02)
-
- 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.
- Shaabani, Ahmad,Hezarkhani, Zeinab,Mofakham, Hamid,Ng, Seikweng
-
p. 1485 - 1492
(2013/08/23)
-
- 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.
- Shaabani, Ahmad,Maleki, Ali,Hajishaabanha, Fatemeh,Mofakham, Hamid,Seyyedhamzeh, Mozhdeh,Manyari, Mojtaba,Ng, Seik Weng
-
experimental part
p. 186 - 190
(2010/10/19)
-
- 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).
- Alizadeh, Abdolali,Zohreh, Nasrin
-
experimental part
p. 1221 - 1226
(2010/08/21)
-
- 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.
- Kidwai, Mazaahir,Mothsra, Poonam
-
p. 817 - 824
(2007/10/03)
-
- 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
- Koizumi, Hitoshi,Itoh, Yuki,Ichikawa, Tsuneki
-
p. 1350 - 1351
(2007/10/03)
-
- 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.
- Kidwai,Ruby,Venkataramanan
-
p. 631 - 634
(2007/10/03)
-
- 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.
- Gedye,Wei
-
p. 525 - 532
(2007/10/03)
-
- 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
- Khan, Mukhtar H.,Bano, Qudsia,Nizamuddin
-
p. 2719 - 2721
(2007/10/03)
-
- An Easy Route to Synthesize 1,5-Arylodiazepin-2-ones
-
A series of 1,5-arylodiazepin-2-ones is prepared by the condensation of the approptiate o-β-arylenediamines with β-ketoesters in xylene under microwave irradiation.The reaction time is shortened to 10 mn, and the products are obtained in high yields.No by products are observed.Specific effects of microwaves are evidenced as no reaction occurs by classical heating in same conditions. - Key Words: Condensation; Microwave; 1,5-Arylodiazepin-2-ones.
- Bougrin, Khalid,Bennani, A. Kella,Tetouani, Souad Fkih,Soufiaoui, Mohamed
-
p. 8373 - 8376
(2007/10/02)
-
- A Novel Syntheses of Pyrano(2,3-c)(1,5)benzodiazepines
-
A novel synthesis of pyrano(2,3-c)(1,5) benzodiazepines from 1H(alkyl)-2,3-dihydro-4-methyl-1,5-benzodiazepin-2-ones and malonitrile or ethyl cyanoacetate is reported.
- Abdel-Ghany, N.,El-Sayed, A.M.,Sultan, A.A.,El-Shafei, A.K.
-
p. 893 - 900
(2007/10/02)
-
- Dehydroacetic acid, precursor of benzodiazepine synthesis
-
Reaction of o-phenylenediamine 1 with dehydracetic acid 2 in different alcohols leads to 2-alkoxycarbonylmethyl 4-methyl 1,5-benzodiazepines 3-7, to 4-acetyl methylene 1,5-benzodiazepin-2-one 8, and to benzimidazoles 9 and 10. This constitutes a novel and efficient synthesis of some benzodiazepine derivatives.
- El Abbassi,Djerrari,Essassi,Fifani
-
p. 7069 - 7070
(2007/10/02)
-
- Synthese et reactivite de nouvelles molecules de type bis--1,n alcanes
-
A number of bis-1,n- alkanes have been prepared by reaction between 4-phenyl (4-cyclopropyl and 4-methyl)-2,3-dihydro 1,5-benzodiazepine 2-one and dihalogenoalkanes X-(CH2)n-X under phase transfer catalysis conditions.The action of hydrazine at different concentration on this structure have been studied.These products have been characterized by NMR 1H, IR, MS and the microanalysis.
- Achour, Redouane,Essassi, El Mokhtar,Zniber, Rachid
-
p. 889 - 896
(2007/10/02)
-
- Synthesis of 2-Substituted 3-Aryl/Heteroaryl-2,3,3a,10-tetrahydro-4-methylpyrazolobenzodiazepines
-
2,3-Dihydro-4-methyl-1H-1,5-benzodiazepin-2-one (1A) and its N-alkyl derivatives (1B,C) undergo condensation with nitroso compounds as well as with a series of aromatic aldehydes to afford 3-anils (2) and 3-arylidene derivatives (3), respectively.Compounds 3 react with hydrazine hydrate in glacial acetic acid or with phenylhydrazine in pyridine to furnish the title compounds (4).The UV-visible spectra of all the compounds in ethanol have been recorded and the absorption bands assigned.
- El-Shafei, A. K.,El-Kashef, H. S.,El-Khawaga, A. M.
-
p. 655 - 657
(2007/10/02)
-
- N-Bridged Heterocycles. Part 5. α,ω-Bis-(2-oxobenzimidazolinyl)-alkanes and -ethers as Selective Ligands for Group-1 and -2 Metals
-
A series of the title compounds (10), (12), and (13) and several analogues were synthesised from the readily available 1-isopropenylbenzimidazolin-2-one.Various substituents were attached to the unsubstituted nitrogen atoms of the benzimidazolinone moieties and the series of products obtained were tested for their complexing ability with group-1 and -2 metal-salts.The isolation of crystalline complexes, the solubilisation of the salts in chloroform by ligand, the i.r. carbonyl absorption shift, and the ion-transport ability of the ligand were examined as an index of complexation.Selective complexation, particularly for calcium, was noted in several cases.
- Meth-Cohn, Otto,Smith, David I.
-
p. 261 - 270
(2007/10/02)
-
- REACTION OF o-PHENYLENEDIAMINE WITH ACETOACETIC AND α-CHLOROACETOACETIC ESTERS
-
The reactivities of acetoacetic and α-chloroacetoacetic esters in the reaction with o-phenylenediamine are compared.In contrast to the available data, it was established that in polyphosphoric acid(PPA) acetoacetic esters is converted to 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one and ethyl 3-(2-aminoanilino)-crotonate, while chloroacetoacetic esters is converted to 2-methylbenzimidazole.At 20 deg C chloroacetoacetic esters is converted to ethyl 2-chloro-3-(2-amino-anilino)crotonate.The conversion of this ester to 2-methyl-3-ethoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one was studied.
- Sheremet, V.I.,Dryuk, V. G.,Solomko, Z. F.,Kremlev, M. M.
-
p. 941 - 945
(2007/10/02)
-
