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Journal articles on the topic 'Azepines'

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Author: Grafiati

Published: 4 June 2021

Last updated: 29 January 2023

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1

Danyliuk, Ivanna, and Mykhailo Vovk. "SYNTHETIC APPROACHES TO HYDROGENIZED PYRIDYL[b]AZEPINE AND THEIR BENZENELYLATED ANALOGUES." Ukrainian Chemistry Journal 86, no. 8 (September 15, 2020): 101–10. http://dx.doi.org/10.33609/2708-129x.86.8.2020.101-110.

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Pyrido[b]azepines are represented in the literature by four types of isomeric structures: pyrido[3,2-b] azepines, pyrido[2,3-b]azepines, pyrido[3,4-b] azepines and pyrido[4,3-b ]azepines. They belong to the structural analogues of 1-benzazepine - an attractive class of heterocycles with a strong pharmacological profile. They are also used as important molecular platforms in the construction of bioactive compounds. Analysis of the literature has shown that compounds that contain the pyrido[b]azepine fragment demonstrate antiviral, antimicrobial, and antitumor activity. They are knownas effective inhibitors of R1P1 kinase, ubiquitin- specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin I type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fundamentally new methods of their synthesis as well as the improvement of known synthetic approaches. In general, among the various methods for the synthesis of hydrogenated pyrido[b] azepines and their benzanelated analogues, priority is currently given to approaches that include the formation of an azepine cycle via the intermolecular formation of C-N and C-C bonds. These mainly include catalytic cyclizations using cobalt, palladium, and rhodium compounds. Reactions of intramolecular radical difluoromethylarylation and diauryl peroxide-initiated radical azepine analelenization of the pyridine fragment are also of great importance. An interesting method for the synthesis of pyrido [2,3-b] azepin-5-one derivatives was developed on the basis of the Friedel-Crafts intramolecular cycloalkylations reaction.

2

Acosta Quintero, Lina M., Isidro Burgos, Alirio Palma, Justo Cobo, and Christopher Glidewell. "A concise, efficient and versatile synthesis of amino-substituted benzo[b]pyrimido[5,4-f]azepines: synthesis and spectroscopic characterization, together with the molecular and supramolecular structures of three products and one intermediate." Acta Crystallographica Section C Structural Chemistry 74, no. 3 (February 21, 2018): 312–20. http://dx.doi.org/10.1107/s2053229618002176.

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A concise, efficient and versatile synthesis of amino-substituted benzo[b]pyrimido[5,4-f]azepines is described: starting from a 5-allyl-4,6-dichloropyrimidine, the synthesis involves base-catalysed aminolysis followed by intramolecular Friedel–Crafts cyclization. Four new amino-substituted benzo[b]pyrimido[5,4-f]azepines are reported, and all the products and reaction intermediates have been fully characterized by IR,1H and13C NMR spectroscopy and mass spectrometry, and the molecular and supramolecular structures of three products and one intermediate have been determined. In each ofN,2,6,11-tetramethyl-N-phenyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-4-amine, C22H24N5, (III), 4-(1H-benzo[d]imidazol-1-yl)-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, which crystallizes as a 0.374-hydrate, C21H19N5·0.374H2O, (VIIIa), and 6,7,9,11-tetramethyl-4-(5-methyl-1H-benzo[d]imidazol-1-yl)-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C24H25N5, (VIIIc), the azepine ring adopts a boat conformation, but with a different configuration at the stereogenic centre in (VIIIc), as compared with (III) and (VIIIa). In the intermediate 5-allyl-6-(1H-benzo[d]imidazol-1-yl)-N-methyl-N-(4-methylphenyl)pyrimidin-4-amine, C22N21N5, (VIIb), the immediate precursor of 4-(1H-benzo[d]imidazol-1-yl)-6,8,11-trimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, (VIIIb), the allyl group is disordered over two sets of atomic sites having occupancies of 0.688 (5) and 0.312 (5). The molecules of (III) are linked into chains by a C—H...π(pyrimidine) hydrogen bond, and those of (VIIb) are linked into complex sheets by three hydrogen bonds, one of the C—H...N type and two of C—H...π(arene) type. The molecules of the organic component in (VIIIa) are linked into a chain of rings by two C—H...π(arene) hydrogen bonds, and these chains are linked into sheets by the water components; a single weak C—H...N hydrogen bond links molecules of (VIIIc) into centrosymmetricR22(10) dimers. Comparisons are made with some related compounds.

3

Acosta Quintero, Lina M., Alirio Palma, Justo Cobo, and Christopher Glidewell. "A concise and efficient concurrent synthesis of 6,11-dihydrodibenzo[b,e]azepines and 5,6,11,12-tetrahydrodibenzo[b,f]azocines and their conversion to 4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylates and N-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines: synthetic sequence, spectroscopic characterization and the structures of two products." Acta Crystallographica Section C Structural Chemistry 75, no. 6 (May 15, 2019): 650–56. http://dx.doi.org/10.1107/s2053229619005746.

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Reaction of 2-allyl-N-benzyl-4-fluoroaniline or 2-allyl-N-benzyl-4-chloroaniline with 98% sulfuric acid leads to the concurrent formation of halogeno-substituted 11-ethyl-6,11-dihydrodibenzo[b,e]azepines, (II), and halogeno-substituted 11-methyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines, (III), in each case in (II):(III) molar ratios of ca 2:1. Further reaction of (II) leads to ethyl 13-ethyl-2-halogeno-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, while acetylation of (III) gives the corresponding N-acetyl derivatives. The dibenzo[b,e]azepine and dibenzo[b,f]azocine ring systems are of importance in forming the core of a variety of bioactive compounds. In ethyl 13-ethyl-2-fluoro-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, C22H20FNO3, (IVa), the azepine ring adopts a conformation close to the twist-boat form, and the molecules are linked into a three-dimensional framework structure by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The azocine ring in 5-acetyl-2-chloro-11-methyl-5,6,11,12-tetrahydrobenzo[b,f]azocine, C18H18ClNO, (Vb), adopts the boat–boat conformation and the molecules are again linked by C—H...O and C—H...π(arene) hydrogen bonds, but this time form a sheet structure.

4

Bozinovic, Nina, Irena Novakovic, Sladjana Kostic-Rajacic, Igor Opsenica, and Bogdan Solaja. "Synthesis and antimicrobial activity of azepine and thiepine derivatives." Journal of the Serbian Chemical Society 80, no. 7 (2015): 839–52. http://dx.doi.org/10.2298/jsc150116013b.

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A series of new 5H-pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The 5H-pyridobenzazepine derivatives showed better antibacterial and antifungal activity than corresponding 5H-dipyridoazepine analogs. Among the synthesized azepines, derivative 8 displayed potent activity against tested bacteria (MIC = 39-78 ?g/mL), while azepine 12 showed promising antifungal activity (MIC = 156-313 ?g/mL). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.

5

Yépes, Andrés F., Alirio Palma, Justo Cobo, and Christopher Glidewell. "Three closely related thienyl-substituted 1,4-epoxynaphtho[1,2-b]azepines: hydrogen-bonded assembly in one, two and three dimensions." Acta Crystallographica Section C Crystal Structure Communications 69, no. 3 (February 20, 2013): 307–12. http://dx.doi.org/10.1107/s0108270113004551.

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(2R,4S)-2-(3-Methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C19H17NOS, (I), crystallizes with a single enantiomer in each crystal, whereas its geometrical isomer (2RS,4SR)-2-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-naphtho[1,2-b]azepine, (II), and (2RS,4SR)-2-(5-bromothiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C18H14BrNOS, (III), both crystallize as racemic mixtures. A combination of one C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds links the molecules of (I) into a three-dimensional framework; the molecules of (II) are linked into aC(4)C(4)[R22(7)] chain of rings by a combination of C—H...N and C—H...O hydrogen bonds; and in (III), whereZ′ = 2, a combination of four C—H...π(arene) hydrogen bonds and two C—H...π(thienyl) hydrogen bonds links the molecules into complex sheets. Comparisons are made with the assembly patterns in some aryl-substituted 1,4-epoxynaphtho[1,2-b]azepines.

6

Fournier, René, Alexa R. Green, Arthur Greenberg, Edward Lee-Ruff, Joel F. Liebman, and Anita Rágyanszki. "Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium upon Formation of Their N-Oxides." Molecules 25, no. 20 (October 16, 2020): 4767. http://dx.doi.org/10.3390/molecules25204767.

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Density functional calculations and up to five different basis sets have been applied to the exploration of the structural, enthalpy and free energy changes upon conversion of the azepine to the corresponding N-oxide. Although it is well known that azepines are typically much more stable than their 7-azanorcaradiene valence isomers, the stabilities are reversed for the corresponding N-oxides. Structural, thermochemical as well as nucleus-independent chemical shift (NICS) criteria are employed to probe the potential aromaticity, antiaromaticity and nonaromaticity of N-methylazepine, its 7-azanorcaradiene valence isomer. For the sake of comparison, analogous studies are performed on N-methylpyrrole and its N-oxide.

7

Zhang, Jinlong, Gaoxi Jiang, Zeng Gao, Jinlong Qian, and Huameng Yang. "Brønsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[f]pyrrolo[1,2-a][1,4]diazepines." Synlett 32, no. 09 (March 27, 2021): 930–34. http://dx.doi.org/10.1055/a-1468-5725.

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AbstractTwo approaches involving intramolecular and intermolecular cyclization, respectively, have been developed for the direct and practical construction of a series of important benzo[f]pyrrolo[1,2-a][1,4]azepines by using Brønsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2-[2-(1H-pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[f]pyrrolo[1,2-a][1,4]azepines in high yields. Furthermore, enantioenriched benzo[f]pyrrolo[1,2-a][1,4]azepines were also obtained by chiral phosphoric acid catalyzed intermolecular addition of [2-(1H-pyrrol-1-yl)phenyl]methanamines to 2-formylbenzoates under mild conditions.

8

Acosta, Lina M., Jorge Jurado, Alirio Palma, Justo Cobo, and Christopher Glidewell. "Five closely related 4-chloro-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepines: similar molecular structures but different supramolecular assemblies." Acta Crystallographica Section C Structural Chemistry 71, no. 12 (November 12, 2015): 1062–68. http://dx.doi.org/10.1107/s2053229615020811.

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Dibenz[b,f]azepine (DBA) is a privileged 6-7-6 tricyclic ring system of importance in both organic and medicinal chemistry. Benzo[b]pyrimido[5,4-f]azepines (BPAs), which also contain a privileged 6-7-6 ring system, are less well investigated, probably because of a lack of straightforward and versatile methods for their synthesis. A simple and versatile synthetic approach to BPAs based on intramolecular Friedel–Crafts alkylation has been developed. A group of closely-related benzo[b]pyrimido[5,4-f]azepine derivatives, namely (6RS)-4-chloro-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C14H14ClN3, (I), (6RS)-4-chloro-8-hydroxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C14H14ClN3O, (II), (6RS)-4-<!?tlsb=-0.14pt>chloro-8-methoxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C15H16ClN3O, (III), and (6RS)-4-chloro-8-methoxy-6,11-dimethyl-2-phenyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, C21H20ClN3O, (IV), has been prepared and their structures compared with the recently published structure [Acosta-Quinteroet al.(2015).Eur. J. Org. Chem.pp. 5360–5369] of (6RS)-4-chloro-2,6,8,11-tetramethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine, (V). All five compounds crystallize as racemic mixtures and they have very similar molecular conformations, with the azepine ring adopting a boat-type conformation in each case, although the orientation of the methoxy substituent in each of (III) and (IV) is different. The supramolecular assemblies in (II) and (IV) depend upon hydrogen bonds of the O—H...N and C—H...π(arene) types, respectively, those in (I) and (V) depend upon π–π stacking interactions involving pairs of pyrimidine rings, and that in (III) depends upon a π–π stacking interaction involving pairs of phenyl rings. Short C—Cl...π(pyrimidine) contacts are present in (I), (II) and (IV) but not in (III) or (V).

9

Khoroshunova, Yulia V., Denis A. Morozov, Andrey I. Taratayko, Sergey A. Dobrynin, Ilia V. Eltsov, Tatyana V. Rybalova, Yulia S. Sotnikova, Dmitriy N. Polovyanenko, Nargiz B. Asanbaeva, and Igor A. Kirilyuk. "The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4." Molecules 26, no. 19 (October 2, 2021): 6000. http://dx.doi.org/10.3390/molecules26196000.

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Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl- 1-azaspiro[4.4]nonanes 1a–d (X = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahydro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocyclopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

10

Potikha, L. M., A. R. Turelyk, and V. A. Kovtunenko. "Synthesis of azepino[1,2-a]benzimidazoles and imidazo[1,2-a]azepines." Chemistry of Heterocyclic Compounds 47, no. 6 (September 2011): 745–54. http://dx.doi.org/10.1007/s10593-011-0829-6.

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11

Panwar, Hemant, and Shishupal Singh. "SYNTHESIS AND CHARACTERIZATION OF 3-ARYL-5H,13AH-QUINOLINO(3,2-F) (1,2,4)TRIAZOLO(4,3-B)(1,2-DIAZA-4-SULPHO)AZEPINES: IN VITRO ANTIFUNGAL AND ANTIBACTERIAL ACTIVITY." Indonesian Journal of Chemistry 11, no. 2 (November 3, 2011): 148–53. http://dx.doi.org/10.22146/ijc.21402.

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3-Aryl-5H,13aH-quinolino(3,2-f)(1,2,4)triazolo(4,3-b)(1,2-diaza-4-sulpho)azepines [2a-i] have been prepared by the cyclisation of 5-aryl-4-amino-3-mercapto-1,2,4-triazole by reaction with 2-chloro-3-formylquinoline in catalytic presence of p-toluene sulphonic acid. All the synthesized compounds have been characterized by elemental and spectral (IR, 1H- NMR and Mass) analysis. Furthermore, all compounds were evaluated for their antibacterial and antifungal activities against selected panel of pathogenic strains. Ampicillin trihydrate and fluconazole were used as standard drugs for antibacterial and antifungal activity, respectively. 3-(2-Chloro)phenyl-5H,13aH-quinolino(3,2-f)(1,2,4)triazolo(4,3-b)(1,2-diaza-4-sulpho)azepine [2h] was found, one of the most potent with lesser toxicity among the all prepared thiazepine derivatives.

12

Döpp, Dietrich, Sabine Jüschke, and Gerald Henkel. "Dicyanomethylene Compounds as Cyanation Reagents." Zeitschrift für Naturforschung B 57, no. 4 (April 1, 2002): 460–70. http://dx.doi.org/10.1515/znb-2002-0412.

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Ethenetetracarbonitrile (2, in benzene solution) and 1,3-dioxoindan-2-ylidene propanedinitrile (4, in ethanol or acetonitrile solution) act on N-aryl-2,3-dihydro-1H-benz[d,e]isoquinolines 6a-d and N-aryl-6,7-dihydro-5H-dibenz[c,e]azepines 11a-d via hydride abstraction followed by addition of cyanide to the iminium carbon atom forming the corresponding 1- and 5-carbonitriles 9a-d and 13a-d, respectively, in moderate to medium yields.Additionally , the known 1,3-dihydroxy-2H-inden-2-ylidenepropanedinitrile 15 and a novel dispirocyclopropane (17) are formed from 4 in the reaction with 6 in acetonitrile and ethanol, respectively. The structures of 17 and 6-(4-methylphenyl)-6,7-dihydro-5H-dibenz[c,e]azepine-5-carbonitrile have been unambiguously confirmed by single-crystal X-ray crystallography.

13

Abell, Andrew D., Andrew J. Phillips, Sangeeta Budhia, Ann M. McNulty, and Blake L. Neubauer. "The Preparation and Biological Activity of Lactam-Based, Non-Steroidal, Inhibitors of Human Type-1 Steroid 5α-Reductase." Australian Journal of Chemistry 51, no. 5 (1998): 389. http://dx.doi.org/10.1071/c97130.

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A Beckmann rearrangement of cis- and trans-fused 3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one oximes has yielded three azepines. An in vitro assay of the azepines and (3aSR,9bSR)-6-methoxy-3-methyl-1,3,3a,4,5,9b-hexahydro-2H-benz[e]indol-2-one, prepared in four steps from naphthalene-1,6-diol, against human type-1 steroid 5α-reductase, revealed the tricyclic five-membered lactam to be a potent inhibitor (IC50 733 nM).

14

Odum, Robert A., and Bernard Schmall. "Photoisomerization of 3H -Azepines." Journal of Chemical Research, no. 8 (1997): 276–77. http://dx.doi.org/10.1039/a702465g.

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15

Nedolya, N. A., O. A. Tarasova, A. I. Albanov, L. V. Klyba, and B. A. Trofimov. "Arylsubstituted 3H-azepines and 4,5-dihydro-3H-azepines from propargylbenzene and isothiocyanates." Russian Journal of General Chemistry 79, no. 5 (May 2009): 1041–44. http://dx.doi.org/10.1134/s1070363209050314.

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16

Gregory, Brian, Eric Bullock, and Teng-Song Chen. "Intramolecular Michael-type additions. IV. Synthesis of 2-azabicyclo[3.2.1]oct-3-enes from 4-chloroalkyl-1,4-dihydropyridines." Canadian Journal of Chemistry 63, no. 4 (April 1, 1985): 843–48. http://dx.doi.org/10.1139/v85-140.

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2-Azabicyclo[3.2.1]oct-3-enes, including examples having a spiro centre at C(8), may be obtained by the reaction of anions derived from 1,3-diketones or cyclopentadiene with 4-chloroalkyl-1,4-dihydropyridines or with azepines. Intermediate 4,5-dihydro-1H-azepines have been isolated under milder conditions. The structures of the bicyclic compounds were established using infrared, ultraviolet, nuclear magnetic resonance, and mass spectrometry. Pharmacological examination of selected compounds revealed low antimicrobial and hypotensive activity.

17

Li, Jin-Heng, De-Lie An, and Jing-Hao Qin. "Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles." Synthesis 52, no. 24 (October 13, 2020): 3818–36. http://dx.doi.org/10.1055/s-0040-1707355.

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Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spiroheterocyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

18

Bonacorso, Helio Gauze, Karl-Ernst Mack, and Franz Effenberger. "Enolethers.XX. Synthesis of azepino[4,5-b]quinoxalines and pyridopyrazino[2,3-d]azepines." Journal of Heterocyclic Chemistry 32, no. 1 (January 1995): 57–64. http://dx.doi.org/10.1002/jhet.5570320110.

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19

Manjappa, Kiran B., Yu-Ting Peng, Teau-Jiuan Liou, and Ding-Yah Yang. "Pseudo three-component approach to coumarin-annulated azepines: synthesis of coumarin[3,4-b]azepines." RSC Advances 7, no. 72 (2017): 45269–73. http://dx.doi.org/10.1039/c7ra09289j.

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A series of coumarin-annulated azepines were synthesized via acid-catalyzed condensation of 3-amino-4-hydroxycoumarin with two equivalents of substituted acetophenones in toluene with moderate to good yields.

20

Maas, Gerhard, Robert Reinhard, and Hans-Georg Herz. "Two-Carbon Ring Enlargement of Five-, Six-, and Seven-Membered 1-Aza-2-vinylcycloalk-2-enes with Dimethyl Acetylenedicarboxylate and Subsequent Thermal Isomerization Reactions." Zeitschrift für Naturforschung B 61, no. 4 (April 1, 2006): 385–95. http://dx.doi.org/10.1515/znb-2006-0404.

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2-Aminodienes, in which the enamine function is incorporated in a five-, six-, or seven-membered ring, react with dimethyl acetylenedicarboxylate in a sequence of [2+2] cycloaddition and electrocyclic ring-opening to form the two-carbon ring expanded unsaturated heterocycles, i.e., 3,4- dicarboxylate substituted 6,7-dihydro-1H-azepines 3, 8 and 21, 1,6,7,8-tetrahydroazocines 22, and 6,7,8,9-tetrahydro-1H-azonines 13. Similarly, 2-[(2-thienyl)ethynyl]-4,5,6,7-tetrahydro-1H-azepine 9 is converted into 2-[(2-thienyl)ethynyl]-6,7,8,9-1H-azonine-3,4-dicarboxylate 10 which was characterized by X-ray structure determination. The eight- and nine-membered azaheterocycles 22 and 13, which have not been isolated, undergo thermal isomerization at elevated temperatures. Thus, ring contraction by a 6π-electrocyclic reaction takes place for N-methyl substituted azonine 13, while the N-allyl moiety of azocines 22 engages in an intramolecular Diels-Alder reaction or a 1,7- electrocyclization reaction

21

Steglich, Wolfgang, Heike Bauer, Michael Große-Bley, Rainer Jeschke, Jakob Josten, and Johann Klein. "Azepine derivatives from toadstools: The development of new syntheses for 3H-and 4H-azepines." Journal of Heterocyclic Chemistry 27, no. 1 (January 1990): 107–10. http://dx.doi.org/10.1002/jhet.5570270109.

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22

Wadepohl, Hubert, and Karl Töllner. "Cyclopentadienylcobalt complexes of some azepines." Journal of Organometallic Chemistry 503, no. 1 (November 1995): 111–15. http://dx.doi.org/10.1016/0022-328x(95)05546-2.

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23

Fjellander, Ester, Zoltán Szabó, and Christina Moberg. "Atropoisomerism in Phosphepines and Azepines." Journal of Organic Chemistry 74, no. 23 (December 4, 2009): 9120–25. http://dx.doi.org/10.1021/jo902047k.

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Demchenko, Sergii, Roman Lesyk, Oleh Yadlovskyi, Johannes Zuegg, Alysha G. Elliott, Iryna Drapak, Yuliia Fedchenkova, Zinaida Suvorova, and Anatolii Demchenko. "Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts." Molecules 26, no. 14 (July 13, 2021): 4253. http://dx.doi.org/10.3390/molecules26144253.

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Abstract:

A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1-[(4-phenoxyphenylcarbamoyl)-methyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chloride 6c possessed a broad activity spectrum towards Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Cryptococcus neoformans, with a high hemolytic activity against human red blood cells and cytotoxicity against HEK-293. However, compound 6c is characterized by a low in vivo toxicity in mice (LD50 > 2000 mg/kg).

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Potikha, L. M., A. R. Turelyk, and V. A. Kovtunenko. "ChemInform Abstract: Synthesis of Azepino[1,2-a]benzimidazoles and Imidazo[1,2-a]azepines." ChemInform 43, no. 14 (March 8, 2012): no. http://dx.doi.org/10.1002/chin.201214174.

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26

Qi, Xu-Kuan, Hong Zhang, Zi-Tong Pan, Rong-Bin Liang, Can-Ming Zhu, Jing-Hong Li, Qing-Xiao Tong, Xue-Wang Gao, Li-Zhu Wu, and Jian-Ji Zhong. "Photoinduced synthesis of fluorinated dibenz[b,e]azepines via radical triggered cyclization." Chemical Communications 55, no. 73 (2019): 10848–51. http://dx.doi.org/10.1039/c9cc04977k.

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27

Boichenko, Maksim A., Olga A. Ivanova, Ivan A. Andreev, Alexey O. Chagarovskiy, Irina I. Levina, Victor B. Rybakov, Dmitriy A. Skvortsov, and Igor V. Trushkov. "Convenient approach to polyoxygenated dibenzo[c,e]pyrrolo[1,2-a]azepines from donor–acceptor cyclopropanes." Organic Chemistry Frontiers 5, no. 19 (2018): 2829–34. http://dx.doi.org/10.1039/c8qo00742j.

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28

Rodríguez-Salamanca, Patricia, Rocío Martín-de la Calle, Verónica Rodríguez, Pedro Merino, Rosario Fernández, José M. Lassaletta, and Valentín Hornillos. "Asymmetric synthesis of dibenzo[b,d]azepines by Cu-catalyzed reductive or borylative cyclization." Chemical Science 12, no. 46 (2021): 15291–97. http://dx.doi.org/10.1039/d1sc04980a.

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29

Mahesh, Kukkamudi, Kanakaraju Ravi, Praveen Kumar Rathod, and Panaganti Leelavathi. "Convenient synthesis of quinoline-fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C–H functionalisation of triazoles." New Journal of Chemistry 44, no. 6 (2020): 2367–73. http://dx.doi.org/10.1039/c9nj05254b.

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30

Zhao, Yulei, Yang Yuan, Murong Xu, Zhong Zheng, Runhua Zhang, and Yanzhong Li. "Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives." Organic & Biomolecular Chemistry 15, no. 30 (2017): 6328–32. http://dx.doi.org/10.1039/c7ob01516j.

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31

Cordonier, Christopher E. J., Kyosuke Satake, Mikihiko Atarashi, Yousuke Kawamoto, Hideki Okamoto, and Masaru Kimura. "Reaction of 2-Methoxy-3H-azepine with NBS: Efficient Synthesis of 2-Substituted 2H-Azepines." Journal of Organic Chemistry 70, no. 9 (April 2005): 3425–36. http://dx.doi.org/10.1021/jo0500232.

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32

Quirós, María Teresa, César Hurtado-Rodrigo, and María Paz Muñoz. "Nucleophile dependent formation of 6- and 7-membered N-heterocycles by platinum-catalysed cyclisation of 1,5-bisallenes." Organic & Biomolecular Chemistry 15, no. 32 (2017): 6731–37. http://dx.doi.org/10.1039/c7ob01469d.

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33

Aubert, Thierry, Michel Farnier, Isabelle Meunier, and Roger Guilard. "Synthesis of dipyrazolo[3,4-b : 4′,3′-f]azepines and dithieno[2,3-b : 3′,2′f]azepines from 1-substituted 2,7-dichloro-4,5-dihydro-1H-azepine-3,6-dicarbaldehydes." J. Chem. Soc., Perkin Trans. 1, no. 11 (1989): 2095–98. http://dx.doi.org/10.1039/p19890002095.

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34

Yang, Fan, Jing Sun, Hong Gao, and Chao-Guo Yan. "Unprecedented formation of spiro[indoline-3,7′-pyrrolo[1,2-a]azepine] from multicomponent reaction of l-proline, isatin and but-2-ynedioate." RSC Advances 5, no. 41 (2015): 32786–94. http://dx.doi.org/10.1039/c5ra04102c.

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35

Šolaja, Bogdan, Nina Božinović, and Igor Opsenica. "Double Palladium-Catalyzed Synthesis of Azepines." Synlett 24, no. 01 (November 27, 2012): 49–52. http://dx.doi.org/10.1055/s-0032-1317667.

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36

ODUM, R. A., and B. SCHMALL. "ChemInform Abstract: Photoisomerization of 3H-Azepines." ChemInform 28, no. 47 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199747140.

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37

Zhou, Ming-Bo, Rui Pi, Fan Teng, Yang Li, and Jin-Heng Li. "Ring-opening formal hetero-[5+2] cycloaddition of 1-tosyl-2,3-dihydro-1H-pyrroles with terminal alkynes: entry to 1-tosyl-2,3-dihydro 2,3-dihydro-1H-azepines." Chemical Communications 55, no. 75 (2019): 11295–98. http://dx.doi.org/10.1039/c9cc05082e.

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38

Acosta Quintero, Lina M., Alirio Palma, Justo Cobo, and Christopher Glidewell. "Six polycyclic pyrimidoazepine derivatives: syntheses, molecular structures and supramolecular assembly." Acta Crystallographica Section C Structural Chemistry 72, no. 4 (March 25, 2016): 346–57. http://dx.doi.org/10.1107/s2053229616004654.

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Abstract:

A versatile synthetic method has been developed for the formation of variously substituted polycyclic pyrimidoazepine derivatives, formed by nucleophilic substitution reactions on the corresponding chloro-substituted compounds; the reactions can be promoted either by conventional heating in basic solutions or by microwave heating in solvent-free systems. Thus, (6RS)-6,11-dimethyl-3,5,6,11-tetrahydro-4H-benzo[b]pyrimido[5,4-f]azepin-4-one, C14H15N3O, (I), was isolated from a solution containing (6RS)-4-chloro-8-hydroxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine and benzene-1,2-diamine; (6RS)-4-butoxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol, C18H23N3O2, (II), was formed by reaction of the corresponding 6-chloro compound with butanol, and (RS)-4-dimethylamino-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol, C16H20N4O, (III), was formed by reaction of the chloro analogue with alkaline dimethylformamide. (6RS)-N-Benzyl-8-methoxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-4-amine, C22H24N4O, (IV), (6RS)-N-benzyl-6-methyl-1,2,6,7-tetrahydropyrimido[5′,4′:6,7]azepino[3,2,1-hi]indol-8-amine, C22H22N4, (V), and (7RS)-N-benzyl-7-methyl-2,3,7,8-tetrahydro-1H-pyrimido[5′,4′:6,7]azepino[3,2,1-ij]quinolin-9-amine, C23H24N4, (VI), were all formed by reaction of the corresponding chloro compounds with benzylamine under microwave irradiation. In each of compounds (I)–(IV) and (VI), the azepine ring adopts a conformation close to the boat form, with the C-methyl group in a quasi-equatorial site, whereas the corresponding ring in (V) adopts a conformation intermediate between the twist-boat and twist-chair forms, with the C-methyl group in a quasi-axial site. No two of the structures of (I)–(VI) exhibit the same range of intermolecular hydrogen bonds: different types of sheet are formed in each of (I), (II), (V) and (VI), and different types of chain in each of (III) and (IV).

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Kočevar, Marijan, Slovenko Polanc, Miha Tisler, and Bojan Vercek. "Pyrano[3,2-c]azepine, a New Heterocyclic System. A New Approach to Pyrido[3,2-c]azepines." HETEROCYCLES 30, no. 1 (1990): 227. http://dx.doi.org/10.3987/com-89-s8.

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40

Syrota, Natalia O., Sergiy V. Kemskiy, Lesya M. Saliyeva, and Mykhailo V. Vovk. "1,2,3-Triazole-4(5)-amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles." Journal of Organic and Pharmaceutical Chemistry 20, no. 2 (July 20, 2022): 27–51. http://dx.doi.org/10.24959/ophcj.22.258512.

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Abstract:

Aim. To analyze and summarize the synthetic potential of 1,2,3-triazole-4(5)-amines as efficient building blocks in the synthesis of triazolo-annulated pyridine, azine and azepine systems.Results and discussion. Original literature sources revealing the synthetic potential of 4(5)-amino functionalized 1,2,3-triazoles as convenient and available building blocks for the preparation of triazolo-annulated pyridines, azines and azepines were analyzed and systematized. Condensation of 1,2,3-triazole-4(5)-amines with methylene active compounds was shown to be a powerful tool for the synthesis of versatile triazolo[4,5-b]pyridines. In turn, the cyclocondensation based on 5-amino-1,2,3-triazole-4-carboxylic acids and their structurally modified derivatives was proven to be a general way for obtaining a number of triazolo[4,5-d]pyrimidine systems. Few representatives of triazolo-annulated pyridazines, 1,3-oxazines and 1,3-thiazines were synthesized by the intramolecular cyclization of the corresponding 4-aryl(carboxy-, aminomethyl)-5-amino-1,2,3-triazoles. The cyclocondensation involving 4,5-diamino-, 4-carbofunctionalized 5-amino-1,2,3-triazoles and 4-amino-5-thiocarboxamido-1,2,3-triazoles was successful for the construction of di-, oxa- and thiazepino-annulated triazoles.Conclusions. The analysis, systematization and summary of the literature regarding the synthetic potential of 1,2,3-triazole-4(5)-amines conclusively demonstrate that these structures are easily available and convenient molecular blocks for the construction of triazolo-annulated pyridine, azine and azepine systems that are important for synthetic and biomedical research.

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Patel, Rahul V., Bhupendra M. Mistry, Riyaz Syed, Nikhil M. Parekh, and Han-Seung Shin. "Pyrrolo[1,2-a]azepines Coupled with Benzothiazole and Fluorinated Aryl Thiourea Scaffolds as Promising Antioxidant and Anticancer Agents." Anti-Cancer Agents in Medicinal Chemistry 19, no. 15 (January 10, 2019): 1855–62. http://dx.doi.org/10.2174/1871520619666190820151043.

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Abstract:

Background: Cancer remains a major health concern throughout history and is responsible for huge numbers of deaths globally. The sensitivity of cancer cells to anticancer drugs is a crucial factor for developing effective treatments. Methods: Pyrrolo[1,2-a]azepines coupled with benzothiazole and fluorinated aryl thiourea scaffolds have been synthesized, and their potential as cytotoxic agents was investigated against different cancer cell lines such as human ovarian cancer (SK-OV-3), cervical cancer (HeLa), colon adenocarcinoma (HT-29) and non-small-cell lung carcinoma (A549). Cytotoxicity of new compounds was confirmed using SRB assay against non-cancer MDCK cell line. In addition, free radical scavenging activity of new pyrrolo[1,2-a]azepines was examined by adopting DPPH and ABTS assays. Results: The results concluded that the presence and position of fluorine atom(s) on the thiourea unit played a significant role in order to gain anticipated efficacies. Results of the cytotoxic assay against non-cancer MDCK cells showed that these new derivatives are safe to study further. New structures were confirmed using spectral and elemental analyses. Conclusion: Pyrrolo[1,2-a]azepines endowed with a benzothiazole entity and fluorinated aryl thiourea substituents were derived aiming to furnish remarkable antioxidant and anticancer activities. New molecules generated showed interesting biological result correlated with the structure and substituent of the final derivatives. Specifically, numbers and position of fluorine atoms on the thiourea unit influenced the biological profile of the mentioned compounds.

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Yang, Tao, Xiaochong Guo, Qin Yin, and Xumu Zhang. "Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines." Chemical Science 10, no. 8 (2019): 2473–77. http://dx.doi.org/10.1039/c8sc04482a.

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Abstract:

An enantioselective synthesis of dibenz[c,e]azepines containing both central and axial chiralities through a one pot N-Boc deprotection/intramolecular asymmetric reductive amination sequence has been achieved with generally excellent enantiocontrol (up to 97% ee).

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Craig, Donald, Samuel R. J. Spreadbury, and Andrew J. P. White. "Synthesis and hetero-Diels–Alder reactions of enantiomerically pure dihydro-1H-azepines." Chemical Communications 56, no. 68 (2020): 9803–6. http://dx.doi.org/10.1039/d0cc04413j.

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Abstract:

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K₂CO₃ gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines.

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El Bialy, Serry A., and Bakr F. Abdel-Wahab. "Synthetic strategies to benzopyrrolo[1,2-a]azepines." Tetrahedron 69, no. 45 (November 2013): 9357–71. http://dx.doi.org/10.1016/j.tet.2013.08.001.

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45

Yempala, Thirumal, Tomer Babu, Dan Gibson, and Bruce K. Cassels. "Dibenzofuran annulated 1-azepines: Synthesis and cytotoxicity." Synthetic Communications 50, no. 3 (December 26, 2019): 438–45. http://dx.doi.org/10.1080/00397911.2019.1703001.

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46

Koch, Rainer, Bernd Wiedel, and Curt Wentrup. "13C NMR calculations on azepines and diazepines." Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1997): 1851–60. http://dx.doi.org/10.1039/a608271h.

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47

Streef, J. W., H. C. van der Plas, N. Nieman, and C. H. Stam. "The reactivity of azepinyl anions, derived from 2-(diethylamino)-5-phenyl-3H-azepines, towards alkylating agents." Recueil des Travaux Chimiques des Pays-Bas 104, no. 6 (September 2, 2010): 166–70. http://dx.doi.org/10.1002/recl.19851040603.

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48

BONACORSO, H. G., K. E. MACK, and F. EFFENBERGER. "ChemInform Abstract: Enolethers. Part 20. Synthesis of Azepino(4,5-b)quinoxalines and Pyridopyrazino(2,3-d)azepines." ChemInform 26, no. 30 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199530187.

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49

Satake, Kyosuke, Christopher Cordonier, Yasuhiro Kubota, Yuexian Jin, and Masaru Kimura. "Plausible Mechanism for the Formation of 2-Methoxy-2H-azepine Derivatives from 3H-Azepines Using Bromine and NBS." HETEROCYCLES 60, no. 10 (2003): 2211. http://dx.doi.org/10.3987/com-03-9851.

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50

de la Fuente, M. Carmen, and Domingo Domínguez. "Synthesis of Pyrrolo- and Pyrido[1,2-a]xanthene [1,9-de]azepines: A Study of the Azepine Ring Construction." Journal of Organic Chemistry 72, no. 23 (November 2007): 8804–10. http://dx.doi.org/10.1021/jo701568w.

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