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Journal articles on the topic 'Diazepin'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Dzedulionytė, Karolina, Melita Veikšaitė, Vít Morávek, et al. "Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones." Molecules 27, no. 24 (2022): 8666. http://dx.doi.org/10.3390/molecules27248666.

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A general approach towards the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-a]indol-1-one and tetrahydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1H-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation—yielding target pyrazolo[1,5-a][1,4]diazepin-4-ones. A straightforward tw

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2

Zemanová, Ivana, Michaela Potančoková, and Renata Gašparová. "Synthesis of 4-OXO-4H-Chromene Derivative with Fused Benzodiazepine Ring." Nova Biotechnologica et Chimica 15, no. 1 (2016): 85–89. http://dx.doi.org/10.1515/nbec-2016-0009.

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Abstract 6-Acetylbenzo[b]chromeno[2,3-e][1,4]diazepin-13(6H)-one 6 was synthesized by reaction of 4- oxo-4H-chromene-3-carboxaldehyde 1 with 1,2-diaminobenzene 2 followed by cyclisation of formed Schiff base 3 and spontaneous oxidation of dihydrodiazepine 4 by air oxygen. Finally, diazepine 5 was acetylated at N(6) by reaction with acetic anhydride.

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3

Addicott, Chris, and Curt Wentrup. "1H-1,3-Diazepines and Ketenimines from Cyanotetrazolopyridines." Australian Journal of Chemistry 61, no. 8 (2008): 592. http://dx.doi.org/10.1071/ch08252.

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Cyano-substituted tetrazolo[1,5-a]pyridines/2-azidopyridines 8T and 15T undergo thermal ring opening to the azides 8A and 15A. Solution photolysis causes nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4,6-tetraenes 10 and 17, which react with alcohols to afford 2-alkoxy-1H-1,3-diazepines, with secondary amines to 2-dialkylamino-5H-1,3-diazepines, and with water to 1,3-diazepin-2-ones (12–14, 19, 21). Argon matrix photolysis of the azides affords the diazacycloheptatetraenes 10 and 17 as principal products together with ring-opened dicyanovinylketenimines 11 and 18. The matr

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4

Odame, F., T. Madanhire, E. C. Hosten, and K. Lobb. "Crystal structure, Hirshfeld surface analysis and computational studies of two benzo[b] [1,4]diazepine derivatives." Журнал структурной химии 64, no. 12 (2023): 119104. http://dx.doi.org/10.26902/jsc_id119104.

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The DFT computational studies, crystal structures and Hirshfeld surface analysis of (E)-4-(2-chlorostyryl)-2,2-dimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine (1) and (E)-4-(2-(2,2-dimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)vinyl)phenol (2) have been presented. The compounds crystallized in the monoclinic space group P21/c with 4 molecules in their unit cells each. The experimental and computed bond lengths and bond angles deviated from each other to some extent but also showed good agreement with each other in some cases. Hirshfeld surface analysis of the compounds provided further inf

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5

Patel, Anil S., Hasmukh R. Khunt, Satish M. Ghelani, Jayesh S. Babariya, Kalpesh V. Vilapara, and Yogesh T. Naliapara. "Two Step One-Pot Synthesis of Novel 5-(4-Fluorophenyl)-1H-Beno[e][1,4]Diazepin-2(3H)-One and it’s Base Catalyzed Transformation to N-Alkyl and C-3 Arylidene Derivatives." International Letters of Chemistry, Physics and Astronomy 30 (March 2014): 106–15. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.30.106.

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We have demonstrated two step one-pot synthesis of novel 5-(4-Fluorophenyl)-1H-Beno[e][1,4]Diazepin-2(3H)-one using 2-Amino-4’-fluorobenzophenone as initial stating material. The small library of N-alkylation and C-3 benzylidene derivatives have been synthesized by base catalyzedreaction of 5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (3) nucleus with various alkyl halides and aromatic aldehydes respectively.

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6

Patel, Anil S., Hasmukh R. Khunt, Satish M. Ghelani, Jayesh S. Babariya, Kalpesh V. Vilapara, and Yogesh T. Naliapara. "Two Step One-Pot Synthesis of Novel 5-(4-Fluorophenyl)-1<i>H</i>-Beno[e][1,4]Diazepin-2(3<i>H</i>)-One and it’s Base Catalyzed Transformation to <i>N</i>-Alkyl and C-3 Arylidene Derivatives." International Letters of Chemistry, Physics and Astronomy 30 (March 12, 2014): 106–15. http://dx.doi.org/10.56431/p-9l954w.

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We have demonstrated two step one-pot synthesis of novel 5-(4-Fluorophenyl)-1H-Beno[e][1,4]Diazepin-2(3H)-one using 2-Amino-4’-fluorobenzophenone as initial stating material. The small library of N-alkylation and C-3 benzylidene derivatives have been synthesized by base catalyzedreaction of 5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (3) nucleus with various alkyl halides and aromatic aldehydes respectively.

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7

Capuano, Ben, Ian T. Crosby, Edward J. Lloyd, Juliette E. Neve, and David A. Taylor. "Aminimides as Potential CNS Acting Agents. I. Design, Synthesis, and Receptor Binding of 4′-Aryl Aminimide Analogues of Clozapine as Prospective Novel Antipsychotics." Australian Journal of Chemistry 60, no. 9 (2007): 673. http://dx.doi.org/10.1071/ch07197.

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A series of substituted 1-[4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)-1-methylhexahydropyrazin-1-ium]-1-aminimide derivatives were designed on the basis of the physicochemical properties of the aminimide functional group and synthesized as potential antipsychotic agents for the treatment of schizophrenia. The target compounds were readily prepared in two steps from clozapine (8-chloro-11-(4-methylpiperazino)-5H-dibenzo[b,e][1,4]diazepine) and involved N-acylation of a common hydrazinium salt intermediate by an acyl chloride or activated ester in the presence of a strong base. The aminimid

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8

Bennamane, Norah, Oualid Talhi, Artur Silva, et al. "Dibenzo[b,e][1,4]diazepin-1-ones and their Ring-Opened Derivatives: Revisited Synthesis, 2D NMR and Crystal Structure." Synlett 28, no. 17 (2017): 2247–52. http://dx.doi.org/10.1055/s-0036-1590306.

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The synthesis of 2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones was revisited and a catalyst-free method was established, by exploring the reactivity of 3-[(2-aminoaryl)amino]dimedones towards carbonylated electrophiles. 2D NMR and single-crystal X-ray diffraction studies were used to characterize the structures unequivocally and to review the mechanism leading to the formation of supposed positional isomers. The action of 3-[(2-aminoaryl)amino]dimedones on chromene-3-carboxylic acid, fumaryl, and oxalyl chloride has led to dibenzo[b,e][1,4]diazepin-1-one ring opening to produce n

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9

Iden, Hassan S., and William D. Lubell. "1,3,5-Trisubstituted 1,4-Diazepin-2-ones." Journal of Organic Chemistry 72, no. 23 (2007): 8980–83. http://dx.doi.org/10.1021/jo701467d.

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10

Xu, Xin-Ming, Sen Chen, Shao-Lei Duan, Xiang-Min Wang, Qian Liu, and Kai Sun. "Synthesis of 1,4-Benzodiazepines via Intramolecular C–N Bond Coupling and Ring Opening of Azetidines." Molecules 30, no. 9 (2025): 2014. https://doi.org/10.3390/molecules30092014.

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A facile and efficient synthesis of functionalized 1,4-benzodiazepine derivatives under mild conditions was developed. The CuI/N,N-dimethylglycine-catalyzed intramolecular cross-coupling reaction of 1-(2-bromobenzyl)azetidine-2-carboxamides proceeded smoothly under mild conditions to provide 1,4,9,10a-tetrahydroazeto[1,2-a]benzo[e][1,4]diazepin-10(2H)-ones. The resulting azetidine-fused 1,4-benzodiazepine compounds underwent consecutive N-methylation with methyl triflate and the opening of the four-membered heterocyclic ring by NaN3, KCN and PhSNa to produce diverse 1,4-benzodiazepine derivati

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11

Nagaraju, Sakkani, Onkara Perumal P., K. Divakar, Banoth Paplal та Dhurke Kashinath. "“On water” synthesis of dibenzo-[1,4]-diazepin-1-ones using l-proline as an organocatalyst and under catalyst-free conditions, and their evaluation as α-glucosidase inhibitors". New Journal of Chemistry 41, № 17 (2017): 8993–9001. http://dx.doi.org/10.1039/c7nj01021d.

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Functionalized dibenzo-[1,4]-diazepin-1-ones are synthesized using the “on-water” concept in the presence of l-proline (organocatalyst; 20 mol%) and under catalyst free conditions (sealed tube) in an aqueous medium.

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12

Naraboli, Basavaraj Shivabasappa, and Biradar Js. "DESIGN AND SYNTHESIS OF BENZODIAZEPINES BEARING BENZIMIDAZOLE/BENZOTHIAZOLE AND INDOLE MOIETIES AS A POTENT ANTIMICROBIAL AND ANTIOXIDANT AGENTS." Asian Journal of Pharmaceutical and Clinical Research 11, no. 1 (2018): 70. http://dx.doi.org/10.22159/ajpcr.2017.v11i1.21947.

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Objective: The present work deals with the synthesis and characterization of biologically active new indole derivatives, namely, 2-((1H-benzo[d] imidazol-2-yl) thio)-N-(4-(4-(1H-indol-3-yl)-8-methyl-1H-benzo[b][1,4]diazepin-2-yl) phenyl) acetamide 3a-d, N-(4-(4-(1H-indol-3-yl)-8-methyl- 1H-benzo[b][1,4]diazepin-2-yl) phenyl)-2-((5-methoxy-1H-benzo[d]imidazol-2-yl) thio) acetamide 4a-d and N-(4-(4-(1H-indol-3-yl)-8-methyl-1H-benzo[b][1,4]diazepin-2-yl) phenyl)-2-(benzo[d]thiazol-2-ylthio) acetamide 5a-d.Methods: All these newly synthesized compounds were screened for their in vitro antimicrobia

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13

Naraboli, Basavaraj Shivabasappa, and Biradar Js. "DESIGN AND SYNTHESIS OF BENZODIAZEPINES BEARING BENZIMIDAZOLE/BENZOTHIAZOLE AND INDOLE MOIETIES AS A POTENT ANTIMICROBIAL AND ANTIOXIDANT AGENTS." Asian Journal of Pharmaceutical and Clinical Research 11, no. 1 (2018): 70. http://dx.doi.org/10.22159/ajpcr.2018.v11i1.21947.

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Objective: The present work deals with the synthesis and characterization of biologically active new indole derivatives, namely, 2-((1H-benzo[d] imidazol-2-yl) thio)-N-(4-(4-(1H-indol-3-yl)-8-methyl-1H-benzo[b][1,4]diazepin-2-yl) phenyl) acetamide 3a-d, N-(4-(4-(1H-indol-3-yl)-8-methyl- 1H-benzo[b][1,4]diazepin-2-yl) phenyl)-2-((5-methoxy-1H-benzo[d]imidazol-2-yl) thio) acetamide 4a-d and N-(4-(4-(1H-indol-3-yl)-8-methyl-1H-benzo[b][1,4]diazepin-2-yl) phenyl)-2-(benzo[d]thiazol-2-ylthio) acetamide 5a-d.Methods: All these newly synthesized compounds were screened for their in vitro antimicrobia

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14

Gherase, Dragos, Jean-Valère Naubron, Christian Roussel, and Michel Giorgi. "XRD and VCD: a marriage of love or convenience? Honeymoon around a cyclic urea derivative." Acta Crystallographica Section C Crystal Structure Communications 68, no. 7 (2012): o247—o252. http://dx.doi.org/10.1107/s010827011202358x.

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The structures and absolute configurations of the enantiomers (3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenyl-4,5,6,7,8,8a-hexahydro-3aH-1,3-dioxolo[4,5-e][1,3]diazepin-6-one 0.33-hydrate, C32H30N2O3·0.33H2O, (Ia), and (3aS,8aS)-2,2-dimethyl-4,4,8,8-tetraphenyl-4,5,6,7,8,8a-hexahydro-3aH-1,3-dioxolo[4,5-e][1,3]diazepin-6-one 0.39-hydrate, C32H30N2O3·0.39H2O, (Ib), have been elucidated unambiguously using the complementary power of single-crystal X-ray diffraction (XRD) and vibrational circular dichroism (VCD). The enantiomers crystallize in the Sohncke space groupP21212 and pack as dimers stabilize

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15

Tolkunov, V. S., A. B. Eres᾽ko, A. V. Mazepa, G. V. Palamarchuk, O. V. Shishkin, and S. V. Tolkunov. "Condensed Diazepines. Synthesis of 1-R-3,4-Dihydro-5H-Benzothieno[2,3-d][1,2]Diazepin-4-Ones." Chemistry of Heterocyclic Compounds 48, no. 9 (2012): 1371–81. http://dx.doi.org/10.1007/s10593-012-1146-4.

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16

Subba Reddy, B. V., Y. Vikram Reddy, and Kiran Kumar Singarapu. "Sequential aza-Piancatelli rearrangement/Friedel–Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives." Organic & Biomolecular Chemistry 14, no. 3 (2016): 1111–16. http://dx.doi.org/10.1039/c5ob01616a.

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2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel–Crafts alkylation with (1H-pyrrol-1-yl)aniline, in the presence of In(OTf)<sub>3</sub> at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds.

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17

Swellmeen, Lubna, Haneen A. Basheer, Amal Uzrail, Haneen Sallam, Yusuf Al-Hiari та Ahlam Alkilani. "Targeting GSK-3β enzyme by diazepino-quinolone derivatives". Tropical Journal of Pharmaceutical Research 21, № 10 (2022): 2147–51. http://dx.doi.org/10.4314/tjpr.v21i10.15.

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Purpose: To synthesize a heterocyclic system containing quinolone and diazepine scaffolds as GSK-3β inhibitor.  Methods: The diazepino-quinoline derivatives were synthesized starting from quinolone nucleus in a simple chemical reaction. The in vitro GSK-3β enzyme assay and MTT assay against cancer cell lines were carried out followed by Z´ı-LYTE GSK-3β assay. Anticancer activity was determined using U-87 glioma cell line.  Results: Diazepino-quinoline derivatives were obtained in a good yield, and compound 102 exhibited significant activity against in vitro GSK-3β (IC50: 0.114 μM),

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18

Keller, Max, Mohan M. Bhadbhade, and Roger W. Read. "Two dibenzodiazepinone molecules with dissimilar dimeric associations and apparent different tautomeric forms." Acta Crystallographica Section C Crystal Structure Communications 68, no. 6 (2012): o240—o246. http://dx.doi.org/10.1107/s0108270112019622.

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In two dibenzodiazepinones,viz.the tricyclic core structure, 5H-dibenzo[b,e]diazepin-11(10H)-one, C13H10N2O, and an acylated derivative, 1-(11-hydroxy-5H-dibenzo[b,e]diazepin-5-yl)-2-{4-[3-(1H-imidazol-1-yl)propyl]piperidin-1-yl}ethanone ethanol monosolvate, C26H29N5O2·C2H5OH, dimeric associationviahydrogen-bond bridging between the cyclic amide entities is evident, but there are considerable differences between the parent compound and the amidated derivative. Highly consistent with reported structures of related tricyclic lactams, two molecules of the nonsubstituted compound are bridged throu

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19

Eresko, A. B., V. S. Tolkunov, and S. V. Tolkunov. "Condensed diazepines. synthesis of 1-aryl-3,5-dihydro-4H-1-benzofuro-[2,3-d][1,2]diazepin-4-ones." Chemistry of Heterocyclic Compounds 46, no. 9 (2010): 1127–32. http://dx.doi.org/10.1007/s10593-010-0637-4.

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20

Reddy, Nalla Ram, Ghanta Mahesh Reddy, and Padi Pratap Reddy. "A new entry to pyrazolo[4,3-e][1,4]diazepines. Facile synthesis of pyrazolo [4,3-e][1,4]diazepin-5,8-diones, 5,6,8-triones and pyrazolo[4,3-e]pyrrolo-[1,2-a][1,4]diazepin-5,10-diones." Journal of Heterocyclic Chemistry 42, no. 4 (2005): 675–78. http://dx.doi.org/10.1002/jhet.5570420429.

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21

Clark, B. A. J., M. C. Evans, D. Lloyd, H. McNab, and S. Parsons. "7-Phenyl-2,3,4,5-tetrahydro-1H-1,4-diazepin-5-one." Acta Crystallographica Section C Crystal Structure Communications 55, no. 10 (1999): 1725–27. http://dx.doi.org/10.1107/s010827019900832x.

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22

Barluenga, José, Miguel Tomás, Alfredo Ballesteros, Jian-She Kong, Santiago García Granda, and Enrique Pérez-Carreño. "A new class of fused 1,4-diazepines: synthesis of substituted 8,8a-dihydrofuro[2,3-b][1,4]diazepin-2-ones." J. Chem. Soc., Chem. Commun., no. 6 (1991): 353–54. http://dx.doi.org/10.1039/c39910000353.

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23

Tolkunov, V. S., A. B. Eres'ko, A. V. Mazepa, G. V. Palamarchuk, O. V. Shishkin, and S. V. Tolkunov. "ChemInform Abstract: Condensed Diazepines. Synthesis of 1-R-3,4-Dihydro-5H-benzothieno[2,3-d][1,2]diazepin-4-ones." ChemInform 44, no. 17 (2013): no. http://dx.doi.org/10.1002/chin.201317177.

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24

El Hafi, Mohamed, Sanae Lahmidi, Lhoussaine El Ghayati, et al. "Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine." Acta Crystallographica Section E Crystallographic Communications 77, no. 8 (2021): 834–38. http://dx.doi.org/10.1107/s2056989021007441.

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The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-2-ylidene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intra

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25

Millini, Roberto, Horst Kisch, and Carl Krüger. "Iron Carbonyl Assisted Synthesis of 1,2-Diazepin-3-ones from Cyclic Diazenes and Alkynes." Zeitschrift für Naturforschung B 40, no. 2 (1985): 187–92. http://dx.doi.org/10.1515/znb-1985-0208.

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Bicyclic 1,2-diazepin-3-ones 1a-c, 2a, c are prepared by an iron carbonyl mediated reaction sequence from alkynes and cyclic 1,2-diazenes. The latter are first converted into hexacarbonyl diiron complexes which react with two molecules of an alkyne to afford tricyclic carbonyl iron compounds I -III. Oxidative degradation with bromine leads to these novel heterocycles whose structure is confirmed by an X-ray analysis of 1b.

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26

Graczyk, Julita, Grzegorz Guzowski, and Izabella Kręźel. "Experimental Studies of the Effect of Cyclic Mitoguazone Analogues on Antineoplastic Activity of Methotrexate." Pteridines 9, no. 4 (1998): 217–21. http://dx.doi.org/10.1515/pteridines.1998.9.4.217.

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Summary In the presented study we tested the effect of the bi- and monocyclic analogues of mitoguazone on neoplastic activity of methotrexate in the model of L1210 leukemia in mice. We have demonstrated that combined therapy involving administration of methotrexate with 2-oxo-propanal bis (4,5,6,7 -tetrahydroIH- l,3-diazepin-2-yl)methylhydrazone dihydroiodide (aM 7) at different doses is more effective than methotrexate monotherapy in mice inoculated with L1210 leukemia.

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27

Lauro, Figueroa-Valverde, Diaz-Cedillo Francisco, Hau-Heredia Lenin, et al. "Design and Synthesis of Diazepin-Steroid Derivative using Some Strategies." Letters in Organic Chemistry 13, no. 1 (2015): 22–32. http://dx.doi.org/10.2174/1570178612666151030214007.

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28

Jasinski, Jerry P., Ray J. Butcher, H. S. Yathirajan, B. Narayana, and K. Prakash Kamath. "5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate." Acta Crystallographica Section E Structure Reports Online 66, no. 5 (2010): o1187—o1188. http://dx.doi.org/10.1107/s160053681001487x.

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29

Golovko, A. I., G. A. Sofronov, and T. V. Klyuntina. "[N-methyl-3H]methylphenazepam, a new ligand for diazepin receptors." Bulletin of Experimental Biology and Medicine 115, no. 4 (1993): 404–5. http://dx.doi.org/10.1007/bf00850915.

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30

Pohlmann, Adriana, Dominique Guillaume, Jean-Charles Quirion, and Henri-Philippe Husson. "Stereoselective synthesis of 1,3-disubstituted hexahydro-1,4-diazepin-2-ones." Tetrahedron Letters 38, no. 33 (1997): 5809–10. http://dx.doi.org/10.1016/s0040-4039(97)01291-4.

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31

Rashed, N., M. Sayed, and E. S. H. El Ashry. "Dibenzo[b,e][1,4]diazepin-1-Ones, Synthesis and Derivatization." Journal of the Chinese Chemical Society 40, no. 2 (1993): 189–94. http://dx.doi.org/10.1002/jccs.199300027.

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32

CHAMMACHE, M., E. M. ESSASSI, M. SALEM, and R. ZNIBER. "ChemInform Abstract: Reactivity of 7-Phenyl-1,4-diazepin-5-one." ChemInform 24, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199331204.

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33

Eresko, A. B., V. S. Tolkunov, and S. V. Tolkunov. "ChemInform Abstract: Condensed Diazepines. Synthesis of 1-Aryl-3,5-dihydro-4H-1-benzofuro[2,3-d][1,2]diazepin-4-ones." ChemInform 42, no. 20 (2011): no. http://dx.doi.org/10.1002/chin.201120171.

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34

Capuano, Ben. "8-Chloro-11-[4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)piperazino]-5H-dibenzo[b,e][1,4]diazepine." Molecules 4, no. 12 (1999): 329–32. http://dx.doi.org/10.3390/41100329.

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35

Gomaa, Mohsen A. M. "Synthesis and Spectral Analysis of 3,4,5-trichloro-6-(dibenzo[d,f][1,3]diazepin-5-yl)-[1,2]-benzoquinones." E-Journal of Chemistry 8, s1 (2011): S91—S96. http://dx.doi.org/10.1155/2011/726420.

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Reaction ofN1,N2-di-(4-methoxyphenyl)- orN1,N2-di-(4-hydroxyphenyl) -amidines (1a-d) with 3,4,5,6-tetrachloro-1,2-benzoquinone (2) in ethyl acetate at room temperature led to formation of new 3,4,5-trichloro-6-(2-hydroxy-6-methyldibenzo[d,f][1,3]diazepin-5-yl[1,2]-benzoquinones (3a-d) in addition toN-aryl-N'-(6,7,8,9-tetrachloro-4-hydroxydibenzo-[1,4]dioxin-2-yl)acetamidines (4a,b). The rational of formation of products3a-dand4a,bwas discussed and structures were confirmed on the basis of elemental analysis and spectral data.

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36

Molteni, Giorgio. "Short Synthesis of Enantiopure Thieno[2,3-f]triazolo[1,5-a][1,4]diazepines and Thieno[2,3-f][1,4]diazepin-5-ones." Journal of Heterocyclic Chemistry 51, S1 (2014): E329—E331. http://dx.doi.org/10.1002/jhet.1859.

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BARLUENGA, J., M. TOMAS, A. BALLESTEROS, J. S. KONG, S. G. GRANDA, and E. PEREZ-CARRENO. "ChemInform Abstract: A New Class of Fused 1,4-Diazepines: Synthesis of Substituted 8,8a- Dihydrofuro(2,3-b)(1,4)diazepin-2-ones." ChemInform 22, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199134188.

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Rashid, Muhammad A., Aisha Ashraf, Sahibzada S. Rehman, Shaukat A. Shahid, Adeel Mahmood, and Muhammad Faruq. "1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance." Current Organic Synthesis 16, no. 5 (2019): 709–29. http://dx.doi.org/10.2174/1570179416666190703113807.

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Background:1,4-Diazepines are two nitrogen containing seven membered heterocyclic compounds and associated with a wide range of biological activities. Due to its medicinal importance, scientists are actively involved in the synthesis, reactions and biological evaluation of 1,4-diazepines since number of decades.Objective:The primary purpose of this review is to discuss the synthetic schemes and reactivity of 1,4- diazepines. This article also describes biological aspects of 1,4-diazepine derivatives, that can be usefully exploited for the pharmaceutical sector.Conclusion:This review summarizes

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Nardi, Monica, Annalisa Cozza, Antonio De Nino, Manuela Oliverio, and Antonio Procopio. "One-Pot Synthesis of Dibenzo[b,e][1,4]diazepin-1-ones." Synthesis 44, no. 05 (2012): 800–804. http://dx.doi.org/10.1055/s-0031-1289691.

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Nouvet, André, Frédéric Lamaty, and René Lazaro. "Synthesis of new perhydro-(1,4)-diazepin-2-ones as constrained peptidomimetics." Tetrahedron Letters 39, no. 15 (1998): 2099–102. http://dx.doi.org/10.1016/s0040-4039(98)00060-4.

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41

Bolli, Martin H., Judith Marfurt, Corinna Grisostomi, et al. "Novel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists." Journal of Medicinal Chemistry 47, no. 11 (2004): 2776–95. http://dx.doi.org/10.1021/jm031115r.

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Fülöpová, Veronika, Tomáš Gucký, Martin Grepl, and Miroslav Soural. "Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives." ACS Combinatorial Science 14, no. 12 (2012): 651–56. http://dx.doi.org/10.1021/co300124q.

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Huang, Xu, and Jiaxi Xu. "Stereospecific synthesis of azeto[2,1-d]- [1,5]benzothiazepin/diazepin-1-ones." Heteroatom Chemistry 14, no. 6 (2003): 564–69. http://dx.doi.org/10.1002/hc.10196.

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44

Fiakpui, Charles Y., and Edward E. Knaus. "An improved synthesis of 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido[3,4-e]-1,4-diazepin-2-one via ortho-directed lithiation of 3-tert-butyl and 3-tert-butoxycarbonylaminopyridine." Canadian Journal of Chemistry 65, no. 6 (1987): 1158–61. http://dx.doi.org/10.1139/v87-193.

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The ortho-directed lithiation of 3-tert-butyl- or 3-tert-butoxycarbonylaminopyridines (3) with alkyllithiums and reaction with N,N-diethylbenzamide followed by acid hydrolysis gave 3-amino-4-benzoylpyridine (6) in good yield. Reaction of BTBO with the glycine derivatives 7a, b and then reaction with 6 afforded 3-alkoxycarbonylaminomethylcarbonylamino-4-benzoylpyridines 8a, b. Acid-catalyzed hydrolysis and cyclization of 8a, b yielded 9, which on methylation gave 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido[3,4-e]-1,4-diazepin-2-one (10) in 36% overall yield from 3a.

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45

D'Souza, Asha M., Daniel J. Rivinoja, Roger J. Mulder, et al. "Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides." Australian Journal of Chemistry 71, no. 9 (2018): 690. http://dx.doi.org/10.1071/ch18196.

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A study of the reactivity of a non-stabilised azomethine ylide, derived from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, with nitro-substituted isatoic anhydrides was undertaken. N-Methyl-4-nitroisatoic anhydride underwent a 1,3-dipolar cycloaddition reaction exclusively at the isatoic anhydride C1-carbonyl group, followed by decarboxylative rearrangement to yield a benzo-1,3-diazepin-5-one derivative. In contrast, N-methyl-5-nitroisatoic anhydride underwent competing cycloaddition processes to the isatoic anhydride C1-carbonyl group and to the nitro-substituted aromatic ring. The d

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Okawa, Tomohiro, and Shoji Eguchi. "Synthesis of pyrazino[2,3-e][1,4]diazepin-5-one and pyrazino[2,3-e]pyrrolo[1,2-a][1,4]diazepin-5-one derivatives via the intramolecular aza-Wittig reaction." Tetrahedron 54, no. 22 (1998): 5853–68. http://dx.doi.org/10.1016/s0040-4020(98)00256-7.

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El Azab, Islam H., and Nadia A. A. Elkanzi. "An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity." Molecules 25, no. 9 (2020): 2051. http://dx.doi.org/10.3390/molecules25092051.

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In search of unprecedented tri and/or tetrapod pharmacophoric conjugates, a series of 32 new 4-ethyl-1H-benzo[b][1,4]diazepin-2(3H)-ones were synthesized and properly elucidated using MS, IR, NMR, and elemental analysis. In vitro investigation of 11 compounds of this series, using a panel of two human tumor cell lines namely; human breast adenocarcinoma (MCF-7), and human colorectal carcinoma (HCT-116), revealed promising cytotoxic activities. Among all synthesized compounds, analogue 9 displayed maximum cytotoxicity with IC50 values of 16.19 ± 1.35 and 17.16 ± 1.54 μM against HCT-116 and MCF-

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Wang, Fang-Ming, Dan Bao, Ming Wang, Ming-Jun Li, Li-Zhuang Chen, and Guang-Fan Han. "Synthesis of new 3-phenyl Substituted Dibenzo-1,4-diazepin-1-one Derivatives." Journal of Chemical Research 38, no. 11 (2014): 664–67. http://dx.doi.org/10.3184/174751914x14138073011066.

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Chechina, N. V., О. F. Kravchuk, I. V. Оmelchenko, О. V. Shishkin, and N. N. Kolos. "The synthesis of novel hexahydrodibenzo[b,e][1,4]diazepin-1-one derivatives." Arkivoc 2015, no. 7 (2015): 77–91. http://dx.doi.org/10.3998/ark.5550190.p009.195.

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Kharaneko, O. I., and S. L. Bogza. "5,7-Dihydropyrrolo[3,4-d][1,2]diazepin-1(2H)-ones. Synthesis and transformations." Russian Journal of Organic Chemistry 52, no. 7 (2016): 1043–49. http://dx.doi.org/10.1134/s1070428016070228.

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