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Journal articles on the topic '4-diazepine'

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Published: 10 March 2023

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1

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 (June 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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2

Stuzhin, Pavel A., Pavel Tarakanov, Svetlana Shiryaeva, Anna Zimenkova, Oscar I. Koifman, Elisa Viola, Maria Pia Donzello, and Claudio Ercolani. "Porphyrazines with annulated diazepine rings 4: Synthesis and properties of MgII tetradiazepinoporphyrazine carrying exocyclic styryl fragments." Journal of Porphyrins and Phthalocyanines 16, no. 07n08 (July 2012): 968–76. http://dx.doi.org/10.1142/s1088424612501052.

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A novel tetradiazepinoporphyrazine MgII complex bearing eight peripheral styryl substituents, [St8TDzPAMg(H2O)] ( St = -CH=CHAr , where Ar = 4-methoxyphenyl ) was prepared by template cyclotetramerization of the corresponding precursor — 5,7-distyryl substituted diazepino-2,3-dicarbonitrile — in the presence of MgII butoxide in n-butanol. UV-visible and 1H NMR spectral data indicate that the complex is strongly aggregated in non-coordinating solvents (dichloromethane, chloroform, benzene), it is dimeric in pyridine, whereas it is predominantly monomeric in dimethylsulfoxide and dimethylformamide. The fluorescence response is high for solutions in which the monomeric form is prevalent, but it is strongly quenched as the content of the dimer is increased. Evidence was obtained that dimerization occurs due to intermolecular hydrogen bonding between acidic CH2 groups in the diazepine ring (6H form) of one molecule with meso- and/or diazepine N atoms of another molecule, dimerization being also contributed by the presence of chlatrated water. In the presence of fluoride anions the dimer is destroyed with formation of the monomeric species, which is changed to the 1H form upon heating, as indicated by 1H NMR spectra.

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3

Tarakanova, Ekaterina N., Pavel A. Tarakanov, Victor E. Pushkarev, and Larisa G. Tomilova. "The first synthesis of sandwich-type complex based on tetradiazepinoporphyrazine ligand." Journal of Porphyrins and Phthalocyanines 18, no. 01n02 (January 2014): 149–54. http://dx.doi.org/10.1142/s1088424613501113.

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Sandwich-type complex based on tetradiazepinoporphyrazine ligand — bis{tetrakis(5,7-di(4-tert-butylphenyl)-6H-1,4-diazepino)[2,3-b,g,l,q]porphyrazinato}lutetium — was synthesized for the first time. The structure of the compound has been confirmed by UV-vis/NIR, 1 H NMR spectroscopy, and MALDI-TOF mass spectrometry data. The introduction of annulated diazepine heterocycles to porphyrazine molecule significantly changes macrocycle reactivity and results in sandwich-type complex under conditions used for the selective synthesis of lanthanide(III) monophthalocyanines.

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4

Kantlehner, Willi, Jochen Mezger, Hansjörg Lehmann, Kai Edelmann, and Wolfgang Frey. "Orthoamide und Iminiumsalze, XCVa. Umsetzungen von Orthoamiden von Alkin-Carbonsäuren mit Acetophenonen und Acetophenon-Phenylhydrazonen." Zeitschrift für Naturforschung B 73, no. 10 (October 25, 2018): 689–701. http://dx.doi.org/10.1515/znb-2018-0065.

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AbstractThe orthoamides of alkyne carboxylic acids 4 react with acetophenones 5 – catalyzed by trialkylborates – to give ketene aminals 6, which can be transformed to 5-amino-5-hydrazino-penta-2,4-dien-1-ones 10 by treatment with 2,4-dinitro-phenylhydrazine. From acetophenone-phenylhydrazones 12 and orthoamides 4 1H-1,2-diazepines 18 (fett) are formed at room temperature, whereas 4-dimethylamino-pyridines 22 are obtained at elevated temperatures. The diazepine 18a is degraded to the pyridine-derivative 22b upon heating. The N-unsubstituted acetophenone-hydrazone 25 reacts with 4c to give amidrazone 26. The constitution of compounds 18a, 22a, 22b, 26 is established by crystal structure analyses.

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5

Meszárosová, Kateřina, Antonín Holý, and Milena Masojídková. "Synthesis of Acyclic Adenine 8,N-Anhydronucleosides." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1109–25. http://dx.doi.org/10.1135/cccc20001109.

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9-(4-Hydroxybutyl)adenine (10) was obtained by reaction of adenine with 4-[(2-tetrahydropyran-2-yl)oxy]butyl chloride (7) in the presence of DBU. 8-Bromo-9-(4-hydroxybutyl)adenine (13) was prepared by bromination of 10 or by alkylation of 8-bromoadenine (11) with 4-bromoethyl acetate followed by methanolysis. Tosylation of compound 13 afforded the 4-tosyloxy derivative 15 which gave on heating with methylamine or cyclopropylamine 6-methyl- (17a) or 6-cyclopropyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17b), while the reaction with hydrazine afforded 7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purine-4,6-diamine (17d). Treatment of compound 13 with thionyl chloride gave 9-(4-chlorobutyl)-8-chloroadenine (18) as the main product which was transformed to 17b, 6-propyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17c) or 7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17e) by reaction with cyclopropylamine, propylamine or ammonia, respectively. Compound 17e was quite stable both in acid and alkaline solutions, at room temperature or at 90 °C. Compound 13 was converted to 9-(4-hydroxybutyl)-8-methylaminoadenine (19) by reaction with methylamine. Compound 19 failed to undergo intramolecular cyclization to diazepine 17a on treatment with diphenyl carbonate, bis(4-nitrophenyl) carbonate or 1,1'-carbonyldiimidazole.

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6

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 aminimides were tested for in vitro activity at the dopamine D4 and serotonin 5-HT2A receptors and were found to possess modest affinity for both receptor systems.

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7

Köllner, Maria Anna, and Detlef Geffken. "Cyclic Oxalylation of Primary N-Substituted Anthranilamides: 1H-Benzo[e][1,4]diazepine-2,3,5(4H)-triones and 11a-Chlorobenzo[ e]oxazolo[3,2-a][1,4]diazepine-2,3,5,11(10H,11aH)-tetraones." Zeitschrift für Naturforschung B 65, no. 9 (September 1, 2010): 1155–60. http://dx.doi.org/10.1515/znb-2010-0916.

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In dependence on the molar ratio, the reaction of primary anthranilamides 3 with oxalyl chloride produced 1H-benzo[e][1,4]diazepine-2,3,5(4H)-triones 4 or 10-substituted 11a-chloro-benzo[e]- oxazolo[3,2-a][1,4]diazepine-2,3,5,11(10H, 11aH)-tetraones 5, the structures of which were unambiguously proven by X-ray diffraction analysis.

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8

El-Ablack, Fawzia Zakaria. "Synthesis of Some New Benzimidazole Derivatives of Pharmaceutical Interest." E-Journal of Chemistry 8, no. 2 (2011): 748–52. http://dx.doi.org/10.1155/2011/723421.

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Reaction of 2-(aminomethyl)benzimidazole dihydrochloride (1) with ethyl acetoacetate was studied to give diazepinone-benzimidazole derivative (2), while, treatment of 1 with phenylhydrazono ethylacetoacetate afforded phenylhydrazino diazepinone derivative (3). On the other hand, reaction of 1 with acetyl acetone resulted in the formation of diazepine derivative (4). The reaction of 1 with ethyl cyanoacetate was studied to give 3-aminodiazepinone derivative (5). Also the reaction of 1 with acetophenone and/or benzophenone has been investigated to give the fused imidazolines 6 and 7 respectively, while the reaction of 1 with cyclopentanone gave benzimidazolyl derivative (8). Treatment of 1 with chloroacetyl chloride gave the fused pyrazinone (9). The treatment of 1 with benzoin gave the derivative (10). The structures of the hitherto unknown compounds have been confirmed from analytical and spectral data. The newly synthesized compounds were screened for antibacterial and antifungal activity.

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9

Krutošíková, Alžbeta, and Mikuláš Hanes. "Substituted 4-Benzylfuro[3,2-b]pyrroles." Collection of Czechoslovak Chemical Communications 57, no. 7 (1992): 1487–94. http://dx.doi.org/10.1135/cccc19921487.

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Preparation of 4-benzylfuro[3,2-b]pyrroles is described and their reactions with selected dienophiles are discussed. Utilization of 4-acetylfuro[3,2-b]pyrroles for preparation of 4-substituted derivatives of furo[3,2-b]pyrrole and the synthesis of ethyl 4-(2- and 4-nitrobenzyl)furo[3,2-b]pyrrole-5-carboxylates for fusing to a 1,4-diazepine system is presented.

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10

Alizadeh, Abdolali, and Parinaz Jamal. "Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-Diamines." Synlett 29, no. 08 (April 4, 2018): 1107–11. http://dx.doi.org/10.1055/s-0036-1591550.

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A two-step sequence was developed for the synthesis of chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazine-13-carboxylates and -diazepine-14-carboxylates by the reaction of substituted dimethyl 2-(3-acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1,n-diamines at room temperature. Advantages of this protocol include ease of handling and the absence of a metal catalyst.

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11

Li, Sainan, Zihui Meng, and Zhibin Xu. "Synthesis of 1, 5, 6, 10 – Tetranitrodecahydro - [1, 4] Diazepino [2, 3-b] Diazepine and Its Thermal Property Research." IOP Conference Series: Materials Science and Engineering 394 (August 7, 2018): 022014. http://dx.doi.org/10.1088/1757-899x/394/2/022014.

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12

BOULOUARD, M., P. DALLEMAGNE, A. ALSAIDI, and S. RAULT. "ChemInform Abstract: Pyrrolothieno(1,4)diazepines. Part 4. First Synthesis of Pyrrolo(1,2-a) thieno(2,3-f)(1,4)diazepine Derivatives." ChemInform 28, no. 25 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199725162.

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13

Wezeman, Tim, Yuling Hu, John McMurtrie, Stefan Bräse, and Kye-Simeon Masters. "Synthesis of Non-Symmetrical and Atropisomeric Dibenzo[1,3]diazepines: Pd/CPhos-Catalysed Direct Arylation of Bis-Aryl Aminals." Australian Journal of Chemistry 68, no. 12 (2015): 1859. http://dx.doi.org/10.1071/ch15465.

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Pd/CPhos-catalysis provides direct arylation/cyclisation of methylene-linked bis-anilines to dibenzo[1,3]diazepines v, which are both non-(C2)-symmetrical and axially chiral. Synthesis of the direct arylation substrates commences with substitution of (N-acyl)anilines to methylene methyl sulfide derivatives, followed by halogenation/de-thiomethylation to N-(chloromethyl)anilines. These are substituted with a second aniline derivative, allowing modular preparation of (ortho-halo)aryl-aminal-linked arenes 4. The C–H functionalising direct arylation conditions were adapted from Fagnou and co-workers: substrates and potassium carbonate were heated in dimethylacetamide in the presence of palladium acetate and an electron-rich and sterically hindered biarylphosphine ligand, here CPhos 5. These conditions delivered the C1-(a)symmetric dibenzo[1,3]diazepine targets, which, due to torsion around the axis of the newly formed biaryl bond, are also intrinsically atropisomeric. The axially twisted scaffold is known to impart special properties to ligands/catalysts when the products are further converted into the corresponding seven-membered ring-containing N-heterocyclic carbenes (e.g. xii and xiv).

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14

Kavitha, C. N., Jerry P. Jasinski, Amanda C. Keeley, H. S. Yathirajan, and A. S. Dayananda. "Olanzapinium dipicrate." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (January 12, 2013): o232—o233. http://dx.doi.org/10.1107/s1600536813000640.

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The asymmetric unit of the title salt [systematic name: 2-methyl-4-(4-methylpiperazin-4-ium-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepinium bis(2,4,6-trinitrophenolate)], C17H22N4S2+·2C6H2N3O7−, consists of a diprotonated olanzapinium cation and two independent picrate anions. In the cation, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character and the N atom in the seven-membered 1,5-diazepine ring, which adopts a boat configuration, is also protonated. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 58.8 (1)°. In one of the picrate anions, a nitro group is disordered over two sets of sites in a 0.748 (5):0.252 (5) ratio, and the benzene ring has a flat envelope conformation with the O−C atom displaced from the mean plane of the other five C atoms [maximum deviation 0.0151 (14) Å] by 0.1449 (14) Å. In the crystal, N—H...O hydrogen bonds and weak intermolecular C—H...S and C—H...O interactions link the components, forming a three-dimensional network.

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15

Werry, Eryn L., William T. Jorgensen, Tristan A. Reekie, Kiyan Afzali, Taylor Garrett, Erick Cn Wong, Oludamilola Awofala, Damien W. Gulliver, Mark Connor, and Michael Kassiou. "Pyrazolo[1, 4]diazepine-based small molecule oxytocin receptor partial agonists." Proceedings for Annual Meeting of The Japanese Pharmacological Society WCP2018 (2018): PO4–1–24. http://dx.doi.org/10.1254/jpssuppl.wcp2018.0_po4-1-24.

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16

Kato, Shiro, Hiroshi Harada, and Toshiya Morie. "Synthesis of 6-amino-1-benzyl-4-methylhexahydro-1H-1,4-diazepine." Journal of Heterocyclic Chemistry 32, no. 2 (March 1995): 637–42. http://dx.doi.org/10.1002/jhet.5570320244.

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17

El Hafi, Mohamed, Sanae Lahmidi, Lhoussaine El Ghayati, Tuncer Hökelek, Joel T. Mague, Bushra Amer, Nada Kheira Sebbar, and El Mokhtar Essassi. "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 (July 27, 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 intramolecular N—HDiazp...ODhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the bc plane are formed by N—HDiazp...ODhydp hydrogen bonds and slipped π–π stacking interactions. The layers are connected by additional slipped π–π stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.8%), H...O/O...H (23.5%) and H...C/C...H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N—H...O hydrogen-bond energy is 57.5 kJ mol−1.

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18

BELTRAME, P., E. CADONI, C. FLORIS, and G. GELLI. "ChemInform Abstract: 1,3-Cycloaddition of Benzonitrile Oxides to Diazepines. Part 2. 1- Ethoxycarbonyl-4-methyl- and 6-methyl-1,2-diazepine." ChemInform 24, no. 49 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199349215.

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19

Hamama, W. S. "Enaminouraciles as Precursors for Synthesis of Pyrimido[4,5-a]pyrimidine- 2,4-diones." Zeitschrift für Naturforschung B 55, no. 5 (May 1, 2000): 443–47. http://dx.doi.org/10.1515/znb-2000-0515.

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The reaction of 6-aminouracil 1 with formaldehyde and secondary amines in ethanol at room temperature gave the corresponding 5-alkylaminomethyl derivatives (2a-c) and bis(4- pyrimidyl) methane (4). Also, Mannich reaction with primary aliphatic and aromatic amines at room temperature afforded pyrimid[4,5-d]pyrimidine (5 and 6). Treatment of 1 with o-phenylenediamine through transamination gave com pound 7 which cyclized through intramolecular Mannich reaction with formalin to yield pyrimido[4,5-e]-[l,4]diazepine (8).

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20

Shablykin, O. V., S. A. Chumachenko, and V. S. Brovarets. "Reactions of New N-(2,2-Dichloro-1-cyanoethenyl)amides with Aliphatic Amines." Russian Journal of General Chemistry 91, no. 9 (September 2021): 1607–12. http://dx.doi.org/10.1134/s1070363221090012.

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Abstract The reaction of the newly synthesized N-(2,2-dichloro-1-cyanoethenyl)prop-2-enamide and 4-chloro-N-(2,2-dichloro-1-cyanoethenyl)butanamide with methylamine or dimethylamine gave rise to previously unknown 5-amino-1,3-oxazole-4-carbonitriles. In the case of the reaction of N-(2,2-dichloro-1-cyanoethenyl)amides with ethylenediamine diacetate, new (Z)-2,3,5,6,7,8-hexahydro-7-oxo-1H-imidazo[1,2-a][1,4]diazepine-9-carbonitrile and 4-chloro-N-(cyano(imidazolidin-2-ylidene)methyl)butanamide were obtained.

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21

Samba, Mohamed, Mohamed Said Minnih, Tuncer Hökelek, Manpreet Kaur, Jerry P. Jasinski, Nada Kheira Sebbar, and El Mokhtar Essassi. "Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione." Acta Crystallographica Section E Crystallographic Communications 75, no. 2 (January 18, 2019): 228–32. http://dx.doi.org/10.1107/s2056989019000689.

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The title compound, C17H18N2O3, is constructed from a benzodiazepine ring system linked to a pendant dihydropyran ring, where the benzene and pendant dihydropyran rings are oriented at a dihedral angle of 15.14 (4)°. Intramolecular N—HDiazp...ODhydpand C—HDiazp...ODhydp(Diazp = diazepine and Dhydp = dihydropyran) hydrogen bonds link the seven-membered diazepine ring to the pendant dihydropyran ring, enclosingS(6) ring motifs. In the crystal, N—HDiazp...ODhydphydrogen bonds link the molecules into infinite chains along [10\overline{1}]. These chains are further linkedviaC—HBnz...ODhydp, C—HDhydp...ODhydpand C—HMth...ODhydp(Bnz = benzene and Mth = methyl) hydrogen bonds, forming a three-dimensional network. The observed weak C—HDiazp... π interaction may further stabilize the structure. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (51.1%), H...C/C...H (25.3%) and H...O/O...H (20.3%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing.

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22

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 (October 25, 1999): 329–32. http://dx.doi.org/10.3390/41100329.

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23

Guillon, Jean, Pascal Sonnet, Patrick Dallemagne, Hugues Miel, Sylvain Rault, Martine Daoust, and Michel Boulouard. "Synthesis of new 6-(4-chlorophenyl)perhydro-1,3-diazepine-2,4-dionesviaureidobutyric acids." Journal of Heterocyclic Chemistry 35, no. 3 (May 1998): 535–39. http://dx.doi.org/10.1002/jhet.5570350308.

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24

El-Saghier, Ahmed M. M., Mansour A. Makhlouf, Naglaa F. H. Mahmoud, and Wedad A. El-Adawish. "A-Alkenoyl Ketene S,S- and N,S-Acetals As Starting For Unexpected and Novel Synthesis of N-Heterocycles." JOURNAL OF ADVANCES IN CHEMISTRY 6, no. 1 (April 10, 2010): 861–72. http://dx.doi.org/10.24297/jac.v6i1.965.

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A series of N-heterocycles such as diazaspiro-[4.5]decane, pyrazolo[4,3-d][1,2]-diazepine, imidazo[3,2,1ij][1,8]naphthyridine derivatives or pyrazolo[3,4-b]pyridin-4-ol were synthesized using a-alkenoyl-, a,a-dialkenoyl ketene-(S,S)-acetals 2a-d, 3a-c or a-dialkenoyl ketene-(N,S)-acetal 12 as starting materials. The biological activity of some new synthesized compounds have been investigated.

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25

Jeyanthi, A., B. Kusuma, and Dayakar Gade. "Synthesis of Diazepine and Thiazepine derivatives of 1H-imidazo [4, 5-b] pyridines (Research Article)." International Journal of Pharmacy and Biological Sciences 11, no. 1 (January 1, 2021): 87–91. http://dx.doi.org/10.21276/ijpbs.2021.11.1.11.

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26

Hormaza, Angelina, Dieter Schollmeyer, and Herbert Meier. "Synthese und Kristallstrukturanalyse eines 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepins / Synthesis and Crystal Structure Analysis of a 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepine." Zeitschrift für Naturforschung B 59, no. 1 (January 1, 2004): 73–76. http://dx.doi.org/10.1515/znb-2004-0111.

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AbstractThe enone unit of chalcones is a synthetically valuable substructure for the formation of heterocycles. Whereas propoxy groups as solubilizing side chains on the phenyl groups do not much affect the generation of pyrazole and pyridine rings, they reduce significantly the yield of the diazepine ring system 4. We attribute this effect to the large twist angles between the ring planes, which are demonstrated by a crystal structure analysis.

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27

Phillips, Oludotun A., KS Keshava Murthy, Charles Y. Fiakpui, and Edward E. Knaus. "Synthesis of 5-phenyl-10-methyl-7H- pyrimido[4,5-f][1,2,4]triazolo[4,3-a][1,4]diazepine and its evaluation as an anticonvulsant agent." Canadian Journal of Chemistry 77, no. 2 (February 1, 1999): 216–22. http://dx.doi.org/10.1139/v98-221.

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The homolytic benzoylation (benzoyl radical) of 5-tert-butylcarbonylaminopyrimidine (6, 1 equiv.) in the presence of benzaldehyde (3 equiv.), water, sulfuric acid, and acetic acid, upon treatment with FeSO4·7H2O (3 equiv.) and 70% t-BuOOH (3 equiv.) at 5-10°C for 10 min afforded a mixture of 4-benzoyl-5-tert-butylcarbonylaminopyrimidine (7, 23%), 4,6-dibenzoyl-5-tert-butylcarbonylaminopyrimidine (8, 44%), and 4-benzoyl-5-tert-butylcarbonylamino-6- methyl pyrimidine (9, 10%). When a similar reaction was performed using 1 equiv. each of PhCHO, FeSO4·7H2O, and t-BuOOH, to prevent formation of the 4,6-dibenzoyl product 8, the monobenzoyl (7, 38%) and 4-benzoyl-6-methyl (9, 6%) products were obtained. A similar homolytic benzoylation of 5-bromopyrimidine (10) using 1.5 equiv. of reagents to generate the benzoyl radical afforded 4-benzoyl-5-bromopyrimidine (11, 61%) as the predominant product. Elaboration of 11 via a six-step reaction sequence afforded 2-hydrazino-5-phenyl-3H-pyrimido[5,4-e][1,4]diazepine (17) in 5.2% overall yield. The acid-catalyzed reaction of 17 with triethyl orthoacetate gave the title compound 5-phenyl-10-methyl-7H-pyrimido[4,5-f][1,2,4]triazolo[4,3-a][1,4]diazepine (18, 62%). The triazolo compound 18 was more potent than valproic acid (Depakene(r)) in both the subcutaneous metrazol (scMet) and maximal electroshock (MES) anticonvulsant screens, and more potent than clonazepam in the MES anticonvulsant screen but less potent than clonazepam in the scMet anticonvulsant screen.Key words: homolytic benzoylation, pyrimidines, pyrimidodiazepines, anticonvulsants.

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28

Jeroundi, Dounia, Ahmed Mazzah, Tuncer Hökelek, El Mestafa El Hadrami, Catherine Renard, Amal Haoudi, and El Mokhtar Essassi. "Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione." Acta Crystallographica Section E Crystallographic Communications 76, no. 4 (March 3, 2020): 467–72. http://dx.doi.org/10.1107/s2056989020002698.

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The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair and boat conformations, respectively. The absolute configuration was assigned on the the basis of L-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C—HBnz...ODiazp and C—HProprg...ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = propargyl) hydrogen bonds link the molecules into two-dimensional networks parallel to the bc plane, enclosing R 4 4(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.8%), H...C/C...H (25.7%) and H...O/O...H (20.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H...O hydrogen-bond energies are 38.8 (for C—HBnz...ODiazp) and 27.1 (for C—HProprg...ODiazp) kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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29

Prabhakar, V., C. Divya Vani, and G. Govindu. "Synthesis, Characterization and Biological Evaluation of Benzo[b][1, 2, 4]triazolo [4, 3-d][1, 4]diazepine Derivatives." Asian Journal of Research in Chemistry 9, no. 2 (2016): 89. http://dx.doi.org/10.5958/0974-4150.2016.00017.1.

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30

Journal, Baghdad Science. "Synthesis and Characterization of Five, Sevene Heterocyclic Membered Rings." Baghdad Science Journal 10, no. 3 (September 1, 2013): 803–17. http://dx.doi.org/10.21123/bsj.10.3.803-817.

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New compounds containing heterocyclic units have been synthesized. These compounds include 2-amino 5- phenyl-1,3,4-thiadiazole (1) as starting material to prepare the Schiff bases 2N[3-nitrobenzylidene -2 hydroxy benzylidene and 4-N,N-dimethyl aminobenzylidene] -5-phenyl-1,3,4-thiadiazole (2abc) , 2N[3-nitrophenyl, 2-hydroxyphenyl or 4-N,N-dimethylaminophenyl] 3-]2-amino-5-phenyl-1,3,4-thiadiazole]-2,3-dihydro-[1,3]oxazepine-benzo-4,7-dione] (3abc), 2N[3-nitrophenyl,2-hydroxyphenyl,4-N,N-dimethylaminophenyl]-3-[2-amino-5-phenyl-1,3,4-thiadiazole-2-yl]-2,3-dihydro-[1,3]oxazepine-4,7-dione[(4abc), 2-N-[3-nitrophenyl, 2-hydroxyphenyl or 4-N,N-dimethylaminophenyl]-3-[2-amino-5-phenyl-1,3,4-thiadiazole-2yl]-1,2,3-trihydro-benzo-[1,2-e][1,3] diazepine-4,7-dione (5abc) ,2N[2-(3-nitrophenyl,2-hydroxyphenyl or 4-N,N-dimethylaminophenyl)]-4-oxo-1,3-thiazolidine-3-yl]-2-amino-5-phenyl-1,3,4-thiadiazole (6abc), 2-N-[5-(3-nitrophenyl,2-hydroxyphenyl or 4-N,N-dimethylaminophenyl)-tetrazolo-1-yl]-2-amino-5-phenyl-1,3,4-thiadiazole (7abc) , 2-N-[5-(3-nitrophenyl,2-hydroxyphenyl or 4-N,N-dimethylaminophenyl)-3-[2-amino-5-phenyl-1,3,4-thiadiazole-2-yl]-2,3-dihydro-[1,3]oxazepine-benzo-4,7-dithione (8abc) , 2-N-[5-(3-nitrophenyl,2-hydroxyphenyl or 4-N,N-dimethylaminophenyl)-3-[2-amino-5-phenyl-1,3,4-thiadiazole-2-yl]-2,3-dihydro-[1,3]oxazepine -4,7-dithione -5-ene (9abc) and 2-N-[5-(3-nitrophenyl,2-hydroxyphenyl or 4-N,N-dimethylaminophenyl)-3-[2-amino-5-phenyl-1,3,4-thiadiazole-2-yl] -1,2,3-trihydro-benzo-[1,2-e][1,3] diazepine -4,7-dithione - (10abc) . the structures of these compounds were characterized by FT-IR, 1H,13C-NMR,Uv/vis spectroscopy and the melting points were determined besides the evaluation of its biological activity.

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31

Główka, M. L. "3-(4-Pyridyl)-5,6,7,8-tetrahydro-9H-1,2,4-triazolo[4,3-a][1,3]diazepine Monohydrate." Acta Crystallographica Section C Crystal Structure Communications 51, no. 2 (February 15, 1995): 285–87. http://dx.doi.org/10.1107/s0108270194006414.

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32

KATO, S., H. HARADA, and T. MORIE. "ChemInform Abstract: Synthesis of 6-Amino-1-benzyl-4-methylhexahydro-1H-1,4-diazepine." ChemInform 26, no. 36 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199536197.

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33

Gann, Austin W., and Partha S. Ray. "Synthesis of 2-amino-6,7,8,9-tetrahydro-6-phenethyl-3H-pyrimido[4,5-e][1,4]diazepin-4(5H)-one: a model for a potential pyrimido[4,5-e][1,4]diazepine-based folate anti-tumor agent." Heterocyclic Communications 21, no. 6 (December 1, 2015): 349–53. http://dx.doi.org/10.1515/hc-2015-0216.

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AbstractReductive cyclization of 2-{N-[(2-amino-4,6-dichloropyrimidin-5-yl)methyl]-N-phenethylamino}acetonitrile (5) with Raney nickel and hydrogen gave the chloropyrimido[4,5-e][1,4]diazepine 3 which could not be converted to 2 via an attempted nucleophilic aromatic substitution with hydroxide. The title compound (2) was prepared, however, by the reductive cyclization of 2-{N-[(2-amino-4-chloro-6-methoxypyrimidin-5-yl)methyl]-N-phenethylamino}acetonitrile (13) followed by treatment with trimethyliodosilane.

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34

Deady, Leslie W., and Clare L. Smith. "Tetracycle Formation from the Reaction of Acetophenones with 1-Aminoanthraquinone, and Further Annulation of Pyridine and Diazepine Rings." Australian Journal of Chemistry 56, no. 12 (2003): 1219. http://dx.doi.org/10.1071/ch03136.

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Acetophenones (H, o-, m-, p-Cl, o-aza) react with aminoanthraquinone in pyridine containing solid sodium hydroxide to form 6-(arylcarbonyl)methyl-2-aryl-7H-naphtho[1,2,3-de]quinolin-7-ones (with the 4-(arylcarbonyl)methyl isomer as minor product). Preformed 7H-benzo[e]perimidin-7-one with acetophenone underwent the second part of this process, i.e. nucleophilic substitution to form 6-phenacyl-7H-benzo-[e]perimidin-7-one. Further reactions are described, including cyclization with ammonium acetate/acetic acid to 2,7-diphenyl-1,6-diazabenzo[e]pyrene and 7-phenyl-1,3,8-triazabenzo[e]pyrene, respectively, and with hydrazine hydrate to 3,8-diphenyl-4H-[1,2]diazepino[3,4-4′,3′ : 4,5-f]naphtho[1,2,3-de]quinoline and 3-phenyl-4H-benzo[e][1,2]diazepino[3,4,5-gh]perimidine.

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35

Journal, Baghdad Science. "Synthesis of substituted (oxazepine, Diazepine, tetrazde) via Schiff Bases for 2- Aminobenzo Thaizole Derivatives." Baghdad Science Journal 10, no. 3 (September 1, 2013): 736–48. http://dx.doi.org/10.21123/bsj.10.3.736-748.

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This work includs synthesis of several Schiff bases by condensation of 6- methoxy – 2- amino benzothiazole with some aldehydes and ketones (2- hydroxyl benzaldehyde, 4- hydroxyl benzaldehyde, 4- N,N –dimethy amino acetophenone, benzophenone) to abtain schiff bases (1-5). These schiff bases were found to react with phthalate anhydride to give oxazepine derivatives (6-10) that were reacted with primary aromatic amines to give Diazepine derivatives (11-15). Besides, we prepared new tetrazole derivatives (16-20) from the reaction of the prepared Schiff bases with sodium azide in the prepared compounds that were characterized by physical properties, FT-IR and some of the 1H-NMR and 13C –NMR spectroscopy.

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36

Aoyagi, Mitsutoshi, Noriaki Minakawa, and Akira Matsuda. "Nucleosides and Nucleotides. 130. The Synthesis of Imidazo[4, 5-e][1, 4] Diazepine Nucleosides FromN1-Substituted Inosines." Nucleosides and Nucleotides 13, no. 6-7 (July 1994): 1535–49. http://dx.doi.org/10.1080/15257779408012169.

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37

Narayana Rao, D. V., A. Raghavendra Guru Prasad, Y. N. Spoorthy, M. Pariplavi, and L. K. Ravindranath. "Synthesis, characterization and biological studies of substituted quinozoline-4-(3H)-ones containing diazepine moiety." Annales Pharmaceutiques Françaises 72, no. 1 (January 2014): 51–58. http://dx.doi.org/10.1016/j.pharma.2013.11.001.

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38

Ponduri, Rajasekhar, Pramod Kumar, and Lakshmana Rao Vadali. "Synthesis and Antimicrobial Activity of New Isoxazolyl Benzo[1, 4] diazepine-5-one Derivatives." ChemistrySelect 3, no. 35 (September 21, 2018): 10108–12. http://dx.doi.org/10.1002/slct.201802371.

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39

Igushkina, Anastasiya V., Alexander A. Golovanov, and Aleksander V. Vasilyev. "Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis." Molecules 27, no. 4 (February 13, 2022): 1256. http://dx.doi.org/10.3390/molecules27041256.

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Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar1C≡CCH=CHC(=O)Ar2], with 3-oxo-3-phenylpropanenitrile (NCCH2COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4–26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon–carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53–98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4H-1,2-diazepine.

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40

Dagar, Anuradha, and Ikyon Kim. "Expansion of diazepine heterocyclic chemical space via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepines." Organic & Biomolecular Chemistry 18, no. 48 (2020): 9836–51. http://dx.doi.org/10.1039/d0ob02002h.

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41

Luan, Lin-bo, Zi-jie Song, Zhi-ming Li, and Quan-rui Wang. "Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepine derivatives by [3+ + 2]-cycloaddition/rearrangement reactions." Beilstein Journal of Organic Chemistry 14 (July 18, 2018): 1826–33. http://dx.doi.org/10.3762/bjoc.14.155.

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Two new series of tricyclic heterocycles, namely 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salts 10 and the related neutral, free bases 13 were synthesized from 4-acetoxy-1-acetyl-4-phenylazo-1,2,3,4-tetrahydroquinolines 8 and nitriles 9 in the presence of aluminium chloride by the [3+ + 2]-cycloaddition reaction of the in situ generated azocarbenium intermediates 14 followed by a ring-expansion rearrangement. In the rearrangement reaction, the phenyl substituent in the initially formed spiro-triazolium adducts 16 underwent a [1,2]-migration from C(3) to the electron-deficient N(2). This led to the ring expansion from 6-membered piperidine to 7-membered diazepine furnishing the tricyclic 1,2,4-triazole-fused 1,4-benzodiazepines.

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42

Mustafa, Amar, N. M. Mikhailova, N. I. Golovtsov, and N. S. Prostakov. "(9-(Pyridazinyl-4)-4-azafluorenes and spiro compounds with 4-azafluorene and indeno[1,2-c]pyridazine (4h-5,6-dihydro-1,2-diazepine) fragments." Chemistry of Heterocyclic Compounds 28, no. 10 (October 1992): 1155–58. http://dx.doi.org/10.1007/bf00529579.

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43

Abdel-Alim, A., M. Hussein, A. El-Shorbagi, A. AbuElMagd, and B. El-Menshawi. "SYNTHESIS AND PHARMACOLOGICAL ACTIVITIES OF NOVEL 1-ALKYL-4-ARYL-6-HYDROXYPERHYDRO1,4-DIAZEPINE-2,3-DIONES." Bulletin of Pharmaceutical Sciences. Assiut 29, no. 2 (December 1, 2006): 253–71. http://dx.doi.org/10.21608/bfsa.2006.65199.

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44

Zalesov, V. V., N. V. Kutkovaya, and L. N. Kurdina. "Synthesis and Pharmacological Activity of 4-Aryl-1,5-benzo[b]diazepine-2-carboxylic Acid Arylamides." Pharmaceutical Chemistry Journal 38, no. 4 (April 2004): 183–85. http://dx.doi.org/10.1023/b:phac.0000038414.14734.c1.

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45

Liu, Jun-Liang, Zhi-Yu Hu, and Qing-Yan Xu. "3′-(3-Hydroxyphenyl)-4-methylspiro[benzo[e][1,4]diazepine-3,2′-oxirane]-2,5(1H,4H)-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (June 18, 2011): o1670. http://dx.doi.org/10.1107/s1600536811022161.

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46

Hodorowicz, Maciej, Katarzyna Stadnicka, Bartosz Trzewik, and Barbara Zaleska. "N-(4-Methylpyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide toluene hemisolvate." Acta Crystallographica Section E Structure Reports Online 63, no. 10 (September 21, 2007): o4115. http://dx.doi.org/10.1107/s1600536807042687.

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47

HARADA, Hiroshi, Toshiya MORIE, and Shiro KATO. "Efficient Synthesis of (R)-6 Benzyloxycarbonylamino-1-methyl-4(3-methylbenzyl)hexahydro-1,4-diazepine. I." CHEMICAL & PHARMACEUTICAL BULLETIN 46, no. 7 (1998): 1160–64. http://dx.doi.org/10.1248/cpb.46.1160.

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48

Dias, Alice M., M. Fernanda, J. R. P. Proença, and Brian L. Booth. "Synthesis of new imidazo[4,5-d][1,3]diazepine derivatives from 5-amino-4-(cyanoformimidoyl)imidazoles." Journal of Heterocyclic Chemistry 33, no. 3 (May 1996): 855–62. http://dx.doi.org/10.1002/jhet.5570330352.

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49

Dzedulionytė, Karolina, Melita Veikšaitė, Vít Morávek, Vida Malinauskienė, Greta Račkauskienė, Algirdas Šačkus, Asta Žukauskaitė, and Eglė Arbačiauskienė. "Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones." Molecules 27, no. 24 (December 7, 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 two-step synthetic approach was applied to expand the current study and successfully functionalize ethyl 1H-indole- and ethyl 1H-benzo[d]imidazole-2-carboxylates. The structures of fused heterocyclic compounds were confirmed by 1H, 13C, and 15N-NMR spectroscopy and HRMS investigation.

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50

Amaghnouje, Amal, Serhii Bohza, Nathalie Bohdan, Imane Es-Safi, Andrii Kyrylchuk, Sanae Achour, Hinde El Fatemi, Dalila Bousta, and Andriy Grafov. "New 2,3-Benzodiazepine Derivative: Synthesis, Activity on Central Nervous System, and Toxicity Study in Mice." Pharmaceuticals 14, no. 8 (August 19, 2021): 814. http://dx.doi.org/10.3390/ph14080814.

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We report the design and synthesis of a new diazepine derivative, 4-(4-methoxyphenyl)-2,3,4,5-tetrahydro-2,3-benzodiazepin-1-one (VBZ102), and the evaluation of its anxiolytic-like profile, memory impairment effect, and toxicity in Swiss mice. VBZ102 was evaluated for central nervous system effects in an open field, light–dark box, and novel object recognition tests under oral administration for acute and sub-acute treatment. We tested the VBZ102 toxicity in mice through a determination of LD50 values and examination of the biochemical and histopathological parameters. The VBZ102 induced an anxiolytic effect at different doses both in the light–dark box and open field tests. Unlike other benzodiazepines (e.g., bromazepam), a sedative effect was noted only after administration of the VBZ102 at 10.0 mg/kg.

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