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Journal articles on the topic 'Diazepine'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

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 (October 17, 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 the abundant literature on synthetic routes, chemical reactions and biological attributes of 1,4-diazepine derivatives. We concluded that 1,4-diazepines have significant importance due to their biological activities like antipsychotic, anxiolytic, anthelmintic, anticonvulsant, antibacterial, antifungal and anticancer. 1,4-diazepine derivatives with significant biological activities could be explored for potential use in the pharmaceutical industries.

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2

Donzello, Maria Pia, Claudio Ercolani, Luisa Mannina, Elisa Viola, Alëna Bubnova, Ol'ga G. Khelevina, and Pavel A. Stuzhin. "Synthesis and Spectroscopic Properties of Low-Symmetry Tribenzoporphyrazines with Annulated 6H-1,4-Diazepine Ring." Australian Journal of Chemistry 61, no. 4 (2008): 262. http://dx.doi.org/10.1071/ch08071.

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Template co-condensation of 2,3-dicyano-5,7-diphenyl-6H-1,4-diazepine 1 with 10-fold molar excess of phthalodinitrile 2 in the presence of MgII propoxide or butoxide in the corresponding alcohol leads to a mixture of MgII-diazepinoporphyrazines 3–6 from which the low symmetry 3:1 species 3, which contains three annulated benzene and one 1,4-diazepine rings, is separated by column chromatography as the aquo complex, [2,4-diphenyltribenzo[b,g,l][1,4]diazepino[2,3-q]porphyrazinato(aquo)magnesium(ii)], [Bz3DzPzMg(H2O)]. The complex 3 can be demetalated in acetic or trifluoroacetic acids under mild conditions with formation of the corresponding free-base [Bz3DzPzH2] 3a. This latter is also formed by co-cyclotetramerization of the same precursors 1 and 2 in the presence of sodium ethoxide in ethanol or lithium butoxide in butanol followed by demetalation of the intermediate disodium or dilithium salts in acid medium. The constitution and structure of the obtained compounds were established on the basis of elemental analysis, mass spectrometry, and 1H NMR spectra. The variable temperature 1H NMR measurements provide evidence that in porphyrazines 3 and 3a the 1,4-diazepine ring exists predominantly in the 6H-form over a wide temperature range. The free energy of activation for the inversion of the 1,4-diazepine ring determined for 3 is 45.6 ± 1.7 kJ mol–1. Solution UV-visible spectra measurements in acidic media (CH2Cl2/CF3COOH) provide evidence that the MgII complex 3 is easily protonated on the meso-N atom of the porphyrazine macrocycle followed by slow demetallation with formation of the free base 3a in its neutral form or as a species protonated on the diazepine ring.

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3

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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4

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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5

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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6

ANGELONI, SILVIA, and CLAUDIO ERCOLANI. "New classes of porphyrazine macrocycles with annulated heterocyclic rings." Journal of Porphyrins and Phthalocyanines 04, no. 05 (August 2000): 474–83. http://dx.doi.org/10.1002/1099-1409(200008)4:5<474::aid-jpp276>3.0.co;2-w.

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The present contribution summarizes the most recent results on the synthesis and chemical physical characterization of the new classes of porphyrazine macrocycles having annulated five- and seven-membered heterocyclic rings, i.e. tetrakis(thiadizole)porphyrazine, TTDPzH 2, tetrakis(selenodiazole)porphyrazine, TSeDPzH 2, tetrakis-2,3-(5,7dipheny-6H-1,4-diazepino)porphyrazine, Ph 8 DzPzH 2, and a number of their metal derivatives, prepared by using, respectively, 3,4-dicyano-1,2,5-thiadiazole, 3,4-dicyano-1,2,5-selenodiazole, and 5,7-diphenyl-2,3-dicyano-6H-1,4-diazepine as monomeric precursors. The available information indicates that, owing to the presence of electron rich and soft atoms ( S , Se ) inserted in the proximity of the porphyrazine core, the TTDPz and TSeDPz macrocycles, closely resembling their phthalocyanine analogues in terms of structural and electronic features and physical behaviour (solubility, thermal stability, vaporizability, etc.), might be promising new materials for applicative properties. Particularly interesting is the operated peripheral ring opening of the TSeDPz macroxycle leading to the formation of octaaminoporphyrazine, followed by its conversion to a tetrakis(pyrazino)porphyrazine. The macrocycles containing the Ph 8 DzPz skeleton, due to the presence of the external non planar diphenyldiazepine units, appear to exhibit a distinct physical behaviour, which can be probably modulated by appropriate alternative substitutions in the 5, 6, and 7 positions of the diazepine rings.

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7

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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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

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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10

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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11

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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12

Aitken, R. Alan, Dheirya K. Sonecha, and Alexandra M. Z. Slawin. "Homopiperazine (Hexahydro-1,4-diazepine)." Molbank 2021, no. 2 (April 10, 2021): M1200. http://dx.doi.org/10.3390/m1200.

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13

Ezhilarasi, K. S., A. Akila, S. Ponnuswamy, B. K. Revathi, and G. Usha. "Crystal structure of 2,2,4-trimethyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine hemihydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 8 (July 15, 2015): o570—o571. http://dx.doi.org/10.1107/s2056989015013201.

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The title compound, C12H18N2·0.5H2O, crystallizes with two independent organic molecules (AandB) in the asymmetric unit, together with a water molecule of crystallization. The diazepine rings in each molecule have a chair conformation. The dihedral angle between benzene ring and the mean plane of the diazepine ring is 21.15 (12)° in moleculeAand 17.42 (11)° in moleculeB. In the crystal, molecules are linked by N—H...O and O—H...N hydrogen bonds, forming zigzag chains propagating along [001].

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14

Beltrame, Paolo, Enzo Cadoni, Maria M. Carnasciali, Gioanna Gelli, Adolfo Lai, Angelo Mugnoli, and Marcella Pani. "1,3-Cycloaddition of Benzonitrile Oxides to Diazepines. I. 1-Ethoxycarbonyl-5-methyl-1,2-diazepine." HETEROCYCLES 34, no. 8 (1992): 1583. http://dx.doi.org/10.3987/com-92-6073.

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15

Tarakanova, Ekaterina N., Stanislav A. Trashin, Anton O. Simakov, Taniyuki Furuyama, Alexander V. Dzuban, Liana N. Inasaridze, Pavel A. Tarakanov, et al. "Double-decker bis(tetradiazepinoporphyrazinato) rare earth complexes: crucial role of intramolecular hydrogen bonding." Dalton Transactions 45, no. 30 (2016): 12041–52. http://dx.doi.org/10.1039/c6dt01779g.

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16

Memoli, Kevin A. "Synthesis of a novel diazepine." Journal of Heterocyclic Chemistry 44, no. 4 (July 2007): 927–28. http://dx.doi.org/10.1002/jhet.5570440430.

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17

Sawanishi, Hiroyuki, and Takashi Tsuchiya. "Regio-selective diazepine formation from 3-azidopyridines: The first examples of monocyclic 2H-1,4-diazepines." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 12 (1985): 5603–5. http://dx.doi.org/10.1248/cpb.33.5603.

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18

Li, Zhenghua, Yaping Zhao, Guilong Tian, Yi He, Gonghua Song, Luc Van Meervelt, and Erik V. Van der Eycken. "Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation." RSC Advances 6, no. 105 (2016): 103601–5. http://dx.doi.org/10.1039/c6ra23180b.

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19

Jaradat, Nidal, Mohammed Hawash, and Murad Abualhasan. "Synthesis and Biological Evaluation of Benzodioxol Derivatives as Cyclooxygenase Inhibitors." Letters in Drug Design & Discovery 17, no. 9 (September 11, 2020): 1117–25. http://dx.doi.org/10.2174/1570180817999200420114402.

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Background: Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used therapeutics; they are competitive inhibitors of cyclooxygenase (COX), the enzyme which mediates the conversion of arachidonic acid to inflammatory prostaglandins. Objective: In this study, new benzodioxol derivatives with different core cycles and functional groups (i.e., aryl acetate, aryl acetic acid and diazepine) were designed, synthesized, identified and evaluated for their analgesic and anti-inflammatory activity, as a preliminary screening study to identify the most potent and more selective groups. Methods: The synthesized compounds were identified using FTIR, HRMS, 1H-NMR and 13C-NMR, and evaluated for their inhibitory activity against ovine COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay kit. Results: Six compounds were synthesized as a preliminary screening study to identify which was the most potent and more selective group towards COX-2 versus COX-1, compared to ketoprofen as non-selective NSAIDs. The compounds have three different groups: aryl acetate, aryl acetic acid and diazepine. The results showed that the most potent compound against the COX- 1 enzyme was 4b (which has diazepine and 2-chlorophenyl) with IC50 = 0.363 μM, and the selectivity ratio of 4b was found to be better than ketoprofen. In contrast, compound 4a (which has diazepine and 3-chlorophenyl) was the most selective with a COX-1/COX-2 ratio value of 0.85 in comparison with a ketoprofen ratio value of 0.20. Conclusion: In general, the synthesized library has moderate activity against both enzymes (i.e., COX-1 and COX-2). Moreover, all six compounds have better COX-2 inhibition selectivity compared to the commercial drug ketoprofen.

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20

Skvortsov, Ivan A., Alina M. Fazlyeva, Ilya A. Khodov, and Pavel A. Stuzhin. "Porphyrazines with annulated diazepine rings. 5. Near-IR-absorbing tetrakis(6,7-dihydro-1H-1,4-diazepino)porphyrazines and effects of acid solvation on their spectral properties." New Journal of Chemistry 44, no. 42 (2020): 18362–71. http://dx.doi.org/10.1039/d0nj04388e.

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21

Boulouard, Michel, Patrick Dallemagne, Abdellah Alsaïdi, and Sylvain Rault. "Pyirolothieno[1,4]diazepines. PartIV. First synthesis of pyrrolo-[1,2-a]thieno[2,3-f][1,4]diazepine Derivatives." Journal of Heterocyclic Chemistry 33, no. 6 (November 1996): 1743–49. http://dx.doi.org/10.1002/jhet.5570330633.

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22

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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23

Daïch, Abdelali, Philippe Ohier, and Bernard Decroix. "Synthesis of a new pyrrolo[1,3]diazepine: 4H-pyrrolo[1,2-a]thieno[2,3-e][1,3]diazepine." Journal of Heterocyclic Chemistry 32, no. 6 (November 1995): 1731–34. http://dx.doi.org/10.1002/jhet.5570320611.

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24

Savelli, Francesco, Alessandro Boido, Iana Vazzana, and Fabio Sparatore. "Tetrahydrocyclopenta[e]pyrido[3,2-b][1,4]diazepine and -cyclopenta[e]pyrido[2,3-b][1,4]diazepine derivatives." Journal of Heterocyclic Chemistry 24, no. 6 (November 1987): 1709–16. http://dx.doi.org/10.1002/jhet.5570240641.

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25

James, Thomas, Paul MacLellan, George M. Burslem, Iain Simpson, J. Andrew Grant, Stuart Warriner, Visuvanathar Sridharan, and Adam Nelson. "A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds." Org. Biomol. Chem. 12, no. 16 (2014): 2584–91. http://dx.doi.org/10.1039/c3ob42512f.

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A modular synthetic approach is described in which combinations of cyclic sulfamidate and hydroxy sulfonamide building blocks may be converted into piperazine, 1,4-diazepine and 1,5-diazocane scaffolds.

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26

Bourcier, Sophie, Yannik Hoppilliard, Taraneh Kargar-Grisel, Jean Marie Pechiné, and Felix Perez. "Do Thermally-Labile 1,4-Benzodiazepines Rearrange under Electrospray and Particle Bombardment?" European Journal of Mass Spectrometry 7, no. 4-5 (August 2001): 359–71. http://dx.doi.org/10.1255/ejms.446.

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Nordiazepam (N), diazepam (D), lorazepam (L), oxazepam (O)and temazepam (T)are 1,4-benzodiazepines. L, O and T are substituted in position 3 of the seven-membered ring by a hydroxyl group and are known to be thermally unstable. N and D are unsubstituted in position 3 and are expected to be thermally stable. We have studied the stability of all these molecules under electrospray conditions and under particle bombardment (MeV ions and UV photons). The fragmentations induced by low energy collision-induced dissociation and high energy collision-activated dissociation of molecules protonated by electrospray were compared with the spontaneous fragmentations of these molecules ionized by particle bombardment. The fragmentation mechanisms were determined using labeled compounds and by means of ab initio calculations using 1,4-diazepine and 3-hydroxy-1,4-diazepine as models. The fragmentation is dramatically dependent upon the substitution in position 3 and upon the internal energy of protonated molecules. At low collision energies, the non-hydroxylated benzodiazepines eliminate CO by opening of the diazepine ring whereas 3-hydroxy-1,4-benzodiazepines eliminate water after ring contraction. At high collision energies, all protonated benzodiazepines eliminate a hydrogen atom by simple bond cleavage. Molecular orbital calculations give arguments in favor of an isomerization in the gas phase of the protonated 3-hydroxybenzodiazepines and of a partial thermal decomposition of 1,4-benzodiazepines occurring before protonation under particle bombardment.

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27

Mojikhalifeh, Sanaz, and Alireza Hasaninejad. "Highly efficient, catalyst-free, one-pot, pseudo-seven-component synthesis of novel poly-substituted pyrazolyl-1,2-diazepine derivatives." Organic Chemistry Frontiers 5, no. 9 (2018): 1516–21. http://dx.doi.org/10.1039/c8qo00210j.

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A novel, green and high yielding preparation of poly-substituted pyrazolyl-1,2-diazepine derivatives is describedviaa one-pot pseudo-seven-component condensation reaction under catalyst-free conditions in EtOH at room temperature.

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28

Kalhapure, Rahul S., Bhushan P. Patil, Mahantesh N. Jadhav, Laxmikant A. Kawle, and Sanjay B. Wagh. "Synthesis of 11-(Piperazin-1-yl)-5H-dibenzo[b,e] [1,4]diazepine on Kilo Scale." E-Journal of Chemistry 8, no. 4 (2011): 1747–49. http://dx.doi.org/10.1155/2011/212014.

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A synthesis of 11-(piperazin-1yl)-5 H-dibenzo[b,e][1,4]diazepine on kilo scale without any chromatographic purification step is reported. Key steps involved are Ullmann condensation, catalytic hydrogenation, and catalyzed cyclization.

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29

BELTRAME, P., E. CADONI, M. CARNASCIALI, G. GELLI, A. LAI, A. MUGNOLI, and M. PANI. "ChemInform Abstract: 1,3-Cycloaddition of Benzonitrile Oxides to Diazepines. Part 1. 1- Ethoxycarbonyl-5-methyl-1,2-diazepine." ChemInform 23, no. 48 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199248218.

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30

RAJALAKSHMI.S, RAJALAKSHMI S., and ARUNA S. ARUNA.S. "Synthesis and Characterization of Some New Substituted Diazepine Derivatives." Global Journal For Research Analysis 3, no. 7 (June 15, 2012): 17–19. http://dx.doi.org/10.15373/22778160/july2014/6.

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31

El-Subbagh, Hussein I., Ghada S. Hassan, Adel S. El-Azab, Alaa A. M. Abdel-Aziz, Adnan A. Kadi, Abdulrahman M. Al-Obaid, Othman A. Al-Shabanah, and Mohamed M. Sayed-Ahmed. "Synthesis and anticonvulsant activity of some new thiazolo[3,2-a][1,3]diazepine, benzo[d]thiazolo[5,2-a][12,6]diazepine and benzo[d]oxazolo[5,2-a][12,6]diazepine analogues." European Journal of Medicinal Chemistry 46, no. 11 (November 2011): 5567–72. http://dx.doi.org/10.1016/j.ejmech.2011.09.021.

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32

Gupta, Sharoni, Pinki B. Punjabi, Chetna Ameta, and Rakshit Ameta. "An Environmentally-Benign Synthesis of Spiro-benzo[1,4]diazepines Using Multi Phase Nano-titania as a Highly Efficient Catalyst via MAOS Technique." Current Organic Synthesis 16, no. 3 (June 17, 2019): 435–43. http://dx.doi.org/10.2174/1570179415666181109095849.

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Aim and Objective: Benzodiazepines and indole fused heterocycles are pharmacologically significant scaffolds. Trivial work on indole fused benzodiazepine compounds is reported in the literature. Hence, it is imperative to explore the synthesis of indole-fused benzodiazepines that may act as a template for biological studies in the future. Hence, in the present work, the synthesis of indole fused benzodiazepine derivatives was undertaken using multi-phase nano-titania as catalyst under microwave irradiation. Materials and Methods: MAOS technique was used to carry out the synthesis of spiro-benzo [1,4]diazepine derivatives in the presence of multiphase nano-titania as a catalyst. Nano-titania was prepared by sol-gel method and characterized by XRD, FT-IR, FESEM, EDS and thermogravimetric techniques. The synthesized spiro-benzo [1,4] diazepine derivatives were identified by physical and spectral methods. Results: Synthesized compounds were obtained in excellent yields in a short span of time. The synthesis was also carried out in the presence of conventional catalysts in addition to nano-titania. Among all the catalysts, the best result was obtained with nano-titania. The amount of nano-titania was optimized to be 0.05g giving 93- 95% yield of products. The study of reusability of nano-titania revealed that it could be reused up to four times with a negligible change in efficiency. Conclusion: The paper reports an efficient, cost-effective and environmentally benign approach for the synthesis of spiro-benzo [1,4] diazepine derivatives in the presence of multiphase nano-titania catalyst under microwave irradiation.

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33

Curtis, NF. "Complexes of Nickel(II) and Copper(II) With 5,5,7-Trimethyl-1,4-Diazepane. Preparation and Kinetics of Acid-Hydrolysis." Australian Journal of Chemistry 39, no. 2 (1986): 239. http://dx.doi.org/10.1071/ch9860239.

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The cyclic diamine 5,5,7-trimethyl-1,4-diazepane, tmdz, is formed by borohydride reduction of 5,7,7-trimethyl-2,3,6,7-tetrahydro-1H-1,4- diazepine , which is formed by a rapid reaction between ethanediamine and 4-methylpent-3-en-2-one. Salts of the cations [Ni( tmdz )2]2+ and [Cu( tmdz )2]2+ were prepared, and their properties are reported. The kinetics of hydrolysis of [Ni( tmdz )2]2+ and [Cu( tmdz )2]2+ and bis (1,4- diazepane )nickel(II), [Ni( dach )2]2+, in aqueous HCl/NaCl media have been studied. Reaction rates are independent of acid concentration over the ranges used . Ni2+,0.1-1 mol l-1 H+ in 1 mol l-1 Cl -, kobs(25°C) = 9.1(1)×10-7 s-1, kobs(50°C) = 2.0(1)×10-5 s-1,ΔH‡96(2)kJ mol-1,0.08-4 mol l-1, H+ in 4 mol l-1 Cl -, kobs (25°pC) = 2.0(3)°10-7 s-1. Cu2+, 0.04-1 mol l-1 H+, 1 mol l-1 Cl -, kobs (25°C) = 0.028(2) s-1, for the displacement of the second ligand . [Ni( dach )2]2+, 0.1-1 mol l-1 H+, 1 mol l-1 Cl -, kobs (25°C) = 0.051(2) s-1. [Ni( tmdz )2]2+ reacts more rapidly with NaOH/edta : 1 mol l-1 NaOH , 0.1 mol l-1, Na2(edtaH2), kobs (25°C) = 7.3(3)×10-3 s-1, 0.5 mol l-1 NaOH , 0.1 mol l-1 Na2(edtaH2), kobs (25°C) = 4.5(3)×10-3 s-1.

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34

Mofakham, Hamid, Ahmad Shaabani, Sajjad Mousavifaraz, Fatemeh Hajishaabanha, Shabnam Shaabani, and Seik Weng Ng. "A novel one-pot pseudo-five-component condensation reaction towards bifunctional diazepine-tetrazole containing compounds: synthesis of 1H-tetrazolyl-1H-1,4-diazepine-2,3-dicarbonitriles and 1H-tetrazolyl-benzo[b][1,4]diazepines." Molecular Diversity 16, no. 2 (May 2012): 351–56. http://dx.doi.org/10.1007/s11030-012-9371-4.

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35

Krieg, Benno, and Ralf Urban. "Synthesen in der Reihe der 1,4-Diazepine." Liebigs Annalen der Chemie 1988, no. 8 (August 16, 1988): 799–801. http://dx.doi.org/10.1002/jlac.198819880816.

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36

Weißenfels, M. "1,5-Benzo[b]diazepine aus ß -Chlorvinylaldehyden." Zeitschrift für Chemie 4, no. 12 (September 2, 2010): 458–59. http://dx.doi.org/10.1002/zfch.19640041208.

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37

Yang, Shu-Ping, Li-Jun Han, Da-Qi Wang, and Tie-Zhu Ding. "2,3-Diphenyl-6,7-dihydro-5H-1,4-diazepine." Acta Crystallographica Section E Structure Reports Online 63, no. 1 (December 8, 2006): o188—o190. http://dx.doi.org/10.1107/s160053680605241x.

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38

Hassan, Alaa A., Aboul-Fetouh E. Mourad, Kamal M. El-Shaieb, and Ashraf H. Abou-Zied. "Ethenetetracarbonitrile and Heterocyclization of Symmetrical Dithiobiurea as well as Thioureidoethylthiourea Derivatives." Zeitschrift für Naturforschung B 59, no. 8 (August 1, 2004): 910–16. http://dx.doi.org/10.1515/znb-2004-0807.

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AbstractN,N’-Disubstituted hydrazinecarbothioamides 6a - c and substituted thioureidoethylthioureas 12a - c react with ethenetetracarbonitrile (TCNE) in ethyl acetate or chlorobenzene to form the derivatives of pyrazole 7, 8; thiadiazole 10, 11 thiadiazepine 9, thiadiazepane 13, imidazolidine 14 and diazepine 15.

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39

DAICH, A., P. OHIER, and B. DECROIX. "ChemInform Abstract: Synthesis of a New Pyrrolo(1,3)diazepine: 4H-Pyrrolo(1,2-a)thieno(2,3- e) (1,3)diazepine." ChemInform 27, no. 20 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199620144.

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40

El-Subbagh, Hussein I., Ghada S. Hassan, Adel S. El-Azab, Alaa A. M. Abdel-Aziz, Adnan A. Kadi, Abdulrahman M. Al-Obaid, Othman A. Al-Shabanah, and Mohamed M. Sayed-Ahmed. "ChemInform Abstract: Synthesis and Anticonvulsant Activity of Some New Thiazolo[3,2-a][1,3]diazepine, Benzo[d]thiazolo[5,2-a][12,6]diazepine and Benzo[d]oxazolo[5,2-a][12,6]diazepine Analogues." ChemInform 43, no. 12 (February 23, 2012): no. http://dx.doi.org/10.1002/chin.201212182.

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41

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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42

Friary, Richard, Andrew T. McPhail, and Vera Seidl. "Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones." Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1133–50. http://dx.doi.org/10.1135/cccc19931133.

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2-methylthio-2-imidazoline and 2-methylthio-1,4,5,6-tetrahydro-2-pyrimidine amidated 2-chloro-3-pyridine- and 2-chloro-3-pyrazinecarbonyl chlorides. The products reacted with aromatic amines forming a series of tricyclic, linearly fused N-aryl pyrimidones. Included among these pyrimidones were 10-aryl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-ones, 11-aryl-2,3,4,11-tetrahydropyrido-[2,3-d]pyrimido[1,2-a]pyrimidin-6(6H)-ones, 10-aryl-2,3-dihydroimidazo[1,2-a]pyrazino[2,3-d]pyrimidin-5(10H)-ones and 11-aryl-2,3,4,11-tetrahydropyrimido-[1,2-a]pyrazino[2,3-d]pyrimidin-6(6H)-ones. 4,5,6,7-Tetrahydro-2-(mythylthio)-1H-1,3-diazepine amidated the ethyl hydrogen carbonate of 2-(phenylamino)-3-pyridinecarboxylic acid, forming 12-phenyl-2,3,4,5-tetrahydropyrido[2',3':4,5]pyrimido[1,2-a][1,3]diazepine-7(12H)-one. A single crystal X-ray analysis and an unambiguous synthesis established the structure of the linearly fused isomer 10-phenyl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-one.

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43

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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44

Král, Vladimír, Ladislav Jelínek, and David Šaman. "Preparation and synthetic utilization of diarylmethylenemalonaldehydes." Collection of Czechoslovak Chemical Communications 54, no. 10 (1989): 2721–30. http://dx.doi.org/10.1135/cccc19892721.

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A general synthetic approach to disubstituted methylenemalonaldehydes consisting in reaction of geminal dihalogeno derivatives with 1,3-bis(dimethylamino)trimethinium perchlorate is described. Solution of the prepared compounds has been determinated by NMR spectroscopy. The prepared compounds were utilized as suitable synthons of pyrazole (XII), 4H-1,2,6-oxadiazine (XIV) and diazepine (XV) derivatives.

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45

Kysil, Volodymyr, Alexander Khvat, Sergey Tsirulnikov, Sergey Tkachenko, and Alexandre Ivachtchenko. "Multicomponent approach to unique 1,4-diazepine-2-amines." Tetrahedron Letters 50, no. 24 (June 2009): 2854–56. http://dx.doi.org/10.1016/j.tetlet.2009.03.141.

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46

Pokhodylo, N. T., O. Ya Shiika, and M. D. Obushak. "Synthesis of thieno[2,3-e][1,4]diazepine derivatives." Russian Journal of Organic Chemistry 50, no. 3 (March 2014): 449–51. http://dx.doi.org/10.1134/s1070428014030282.

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47

Ozer, Merve Sinem, Gani Koza, Ertan Sahin, and Metin Balci. "Furo- and thieno-fused 1,3-diazepine-4,6-diones." Tetrahedron Letters 54, no. 48 (November 2013): 6553–56. http://dx.doi.org/10.1016/j.tetlet.2013.09.103.

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48

Insuasty, Braulio, Angélica García, Juan Bueno, Jairo Quiroga, Rodrigo Abonia, and Alejandro Ortiz. "Antimycobacterial Activity of Pyrimido[4,5-b]diazepine Derivatives." Archiv der Pharmazie 345, no. 9 (June 25, 2012): 739–44. http://dx.doi.org/10.1002/ardp.201100433.

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49

Ivanov, E. I., A. A. Polishchuk, and A. V. Mazepa. "New synthesis of imidazo[4,5-e][1,3]diazepine." Chemistry of Heterocyclic Compounds 28, no. 9 (September 1992): 1006–8. http://dx.doi.org/10.1007/bf00531476.

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50

Borowiak, T., and I. Wolska. "Structure of 6,6-diethylperhydro-1,4-diazepine-5,7-dione." Acta Crystallographica Section C Crystal Structure Communications 45, no. 6 (June 15, 1989): 936–38. http://dx.doi.org/10.1107/s0108270188014039.

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