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Journal articles on the topic 'Diazocane'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

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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2

Rapelli, Chandrashekhar, Balasubramanian Sridhar, and B. V. Subba Reddy. "Correction: Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds." Organic & Biomolecular Chemistry 18, no. 36 (2020): 7224. http://dx.doi.org/10.1039/d0ob90122a.

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Correction for ‘Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds’ by Chandrashekhar Rapelli et al., Org. Biomol. Chem., 2020, 18, 6710–6715, DOI: 10.1039/D0OB01384F.

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3

Rapelli, Chandrashekhar, Balasubramanian Sridhar, and B. V. Subba Reddy. "Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds." Organic & Biomolecular Chemistry 18, no. 34 (2020): 6710–15. http://dx.doi.org/10.1039/d0ob01384f.

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A tandem Prins strategy has been developed for the first time to produce a novel class of spiro-1,4-diazocane derivatives by the condensation of indole tethered γ-hydroxyolefin with aldehydes using BF₃·OEt₂ at −40 °C in dichloromethane.

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4

Van Meervelt, L., and P. Kong Thoo Lin. "5,8-Bis(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-1,4-dioxa-5,8-diazocane." Acta Crystallographica Section C Crystal Structure Communications 53, no. 8 (August 15, 1997): 1131–33. http://dx.doi.org/10.1107/s0108270197003806.

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5

Heintze, Linda, Dorian Schmidt, Theo Rodat, Lydia Witt, Julia Ewert, Malte Kriegs, Rainer Herges, and Christian Peifer. "Photoswitchable Azo- and Diazocine-Functionalized Derivatives of the VEGFR-2 Inhibitor Axitinib." International Journal of Molecular Sciences 21, no. 23 (November 25, 2020): 8961. http://dx.doi.org/10.3390/ijms21238961.

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In this study, we aimed at the application of the concept of photopharmacology to the approved vascular endothelial growth factor receptor (VEGFR)-2 kinase inhibitor axitinib. In a previous study, we found out that the photoisomerization of axitinib’s stilbene-like double bond is unidirectional in aqueous solution due to a competing irreversible [2+2]-cycloaddition. Therefore, we next set out to azologize axitinib by means of incorporating azobenzenes as well as diazocine moieties as photoresponsive elements. Conceptually, diazocines (bridged azobenzenes) show favorable photoswitching properties compared to standard azobenzenes because the thermodynamically stable Z-isomer usually is bioinactive, and back isomerization from the bioactive E-isomer occurs thermally. Here, we report on the development of different sulfur–diazocines and carbon–diazocines attached to the axitinib pharmacophore that allow switching the VEGFR-2 activity reversibly. For the best sulfur–diazocine, we could verify in a VEGFR-2 kinase assay that the Z-isomer is biologically inactive (IC50 >> 10,000 nM), while significant VEGFR-2 inhibition can be observed after irradiation with blue light (405 nm), resulting in an IC50 value of 214 nM. In summary, we could successfully develop reversibly photoswitchable kinase inhibitors that exhibit more than 40-fold differences in biological activities upon irradiation. Moreover, we demonstrate the potential advantage of diazocine photoswitches over standard azobenzenes.

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6

Cai, Xiao-Qing, Ai-Li Liu, Xiao-Wei Yan, Ke-Jian Zhao, Mei-Rong Li, and Xiao-Nuan Xie. "Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2." Zeitschrift für Kristallographie - New Crystal Structures 224, no. 2 (June 2009): 224–26. http://dx.doi.org/10.1524/ncrs.2009.0100.

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7

Cai, Xiao-Qing, Ai-Li Liu, Xiao-Wei Yan, Ke-Jian Zhao, Mei-Rong Li, and Xiao-Nuan Xie. "Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2." Zeitschrift für Kristallographie - New Crystal Structures 224, no. 1-4 (April 2009): 224. http://dx.doi.org/10.1524/ncrs.2009.224.14.224.

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8

Cai, Xiao-Qing, Ai-Li Liu, Xiao-Wei Yan, Ke-Jian Zhao, Mei-Rong Li, and Xiao-Nuan Xie. "Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2." Zeitschrift für Kristallographie - New Crystal Structures 224, no. 1-4 (April 2009): 234–36. http://dx.doi.org/10.1524/ncrs.2009.224.14.234.

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9

Schehr, Miriam, Daniel Hugenbusch, Tobias Moje, Christian Näther, and Rainer Herges. "Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer–Mills reactions." Beilstein Journal of Organic Chemistry 14 (November 7, 2018): 2799–804. http://dx.doi.org/10.3762/bjoc.14.257.

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Herein we report a reliable method to synthesize mono-functionalized S-diazocines in reproducible yields via intramolecular Baeyer–Mills reactions. Diazocines exhibit excellent photoswitchable properties. As opposed to azobenzenes they are more stable in their cis configuration. Particularly in photopharmacology mono-functionalized diazocines should be potentially useful and superior to the frequently used azobenzenes because the sterically more demanding cis configuration should be inactive, and the slender trans configuration should fit in a tight binding pocket of a receptor. Hence, it should be possible to administer the stabile inactive compound and switch it on at the site of illness with visible light. To date only a limited number of diazocine derivatives have been published of which most are symmetrically functionalized. Using the Baeyer–Mills reaction for the synthesis of diazocines opens a novel and convenient access to unsymmetrically substituted diazocines.

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10

VAN MEERVELT, L., and P. KONG THOO LIN. "ChemInform Abstract: 5,8-Bis(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-1,4-dioxa-5,8- diazocane (V)." ChemInform 28, no. 48 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199748206.

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11

Xu, Qiang, Guo Qiang Li, and Jiang Ping Meng. "Crystal structure of [2,2'-(1,5-diazocane-1,5-diyl)diethanamine-κ4N]- nickel(II) diperchlorate, C10H24Cl2N4NiO8." Zeitschrift für Kristallographie - New Crystal Structures 230, no. 3 (September 1, 2015): 231–32. http://dx.doi.org/10.1515/ncrs-2014-9148.

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12

Collier, W., LS Curtis, NF Curtis, and IJ Pomer. "Kinetics of Acid-Hydrolysis of Nickel(II) and Copper(II) Compounds With the Cyclic Diamines 1,5-Diazocane and 4,4-Dimethyl-7-(5,5,7-trimethyl-1,4-diazepan-1-Yl)-5-azaheptan-2-ol." Australian Journal of Chemistry 42, no. 9 (1989): 1611. http://dx.doi.org/10.1071/ch9891611.

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The kinetics of acid-promoted hydrolysis reactions of nickel(II) and copper(ll) complexes of the cyclic diamines 1,5-diazocane ( daco ) and 4,4-dimethyl-7-(5,5,7-trimethyl-1,4-diazepan-1-yl)-5-azaheptan-2-ol (pyaz) in NaCl/HCl media ([Cl-] = 2 mol dm-3) are reported. For [Ni( daco )2]2+, beyond small [H+], an acid-limited rate constant of 2.0×10-5 S-l, involving dissociation of the first daco ligand, and for [Cu( daco )2]2+ a similarly acid-limited rate constant of 1.5×10-2 s-l, involving dissociation of the second daco ligand, were measured at 50°C. For [Ni( pyaz )]2+ and [Cu ( pyaz )2+ the rates of the hydrolysis reactions are again acid-limited, effectively independent of acid with rate constant of 1.0×10-2 s-1 for [Ni( pyaz )]2+ while for [Cu( pyaz )]2+ the rate follows the expression kobs , = 6.0×10-2[H+]/(l+4.6[H+]) S-l, both measured at 25°C.

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13

Zou, Yang, Tao Zhang, Guannan Wang, Mengwen Zhou, Yabo Xiong, Shaoyun Huang, Houbin Li, and Xinghai Liu. "Microfluidic continuous flow synthesis of 1,5-ditosyl-1,5-diazocane-3,7-dione using response surface methodology." Journal of Industrial and Engineering Chemistry 82 (February 2020): 113–21. http://dx.doi.org/10.1016/j.jiec.2019.10.002.

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14

AVERSA, M. C., P. BONACCORSI, and P. GIANNETTO. "ChemInform Abstract: 1,5-Bis(2-hydroxybenzyl)-1,5-diazocane-2,6-diones from 3-(2- Hydroxybenzylamino)alkanecarboxylic Acids." ChemInform 25, no. 16 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199416207.

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15

Omondi, Brian A., Hirotaka Okabe, Yoshiki Hidaka, and Kazuhiro Hara. "Poly (1, 4-diazocane-5, 8-dione) macrocyclic-functionalized hydrogel for high selectivity transition metal ion adsorption." Reactive and Functional Polymers 125 (April 2018): 11–19. http://dx.doi.org/10.1016/j.reactfunctpolym.2018.02.003.

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16

Crestey, François, Matthias Witt, Jerzy W. Jaroszewski, and Henrik Franzyk. "Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks." Journal of Organic Chemistry 74, no. 15 (August 7, 2009): 5652–55. http://dx.doi.org/10.1021/jo900441s.

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17

Shvydenko, Tetiana, Kostiantyn Nazarenko, Kostiantyn Shvydenko, Sergey Boron, Oleksii Gutov, Andrey Tolmachev, and Aleksandr Kostyuk. "Reduction of imidazolium salts – An approach to diazocines and diazocanes." Tetrahedron 73, no. 49 (December 2017): 6942–53. http://dx.doi.org/10.1016/j.tet.2017.10.053.

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18

Crestey, Francois, Matthias Witt, Jerzy W. Jaroszewski, and Henrik Franzyk. "ChemInform Abstract: Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks." ChemInform 41, no. 1 (January 5, 2010): no. http://dx.doi.org/10.1002/chin.201001176.

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19

Sell, Hanno, Christian Näther, and Rainer Herges. "Amino-substituted diazocines as pincer-type photochromic switches." Beilstein Journal of Organic Chemistry 9 (January 2, 2013): 1–7. http://dx.doi.org/10.3762/bjoc.9.1.

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Azobenzenes are robust, reliable, and easy to synthesize photochromic switches. However, their high conformational flexibility is a disadvantage in machine-like applications. The almost free rotation of the phenyl groups can be restricted by bridging two ortho positions with a CH2CH2 group, as realized in the dihydrodibenzo diazocine framework. We present the synthesis and properties of 3,3’-amino- and 3,3’-acetamido substituted diazocines. Upon irradiation with light of 405 and 530 nm they isomerize from the cis to the trans configuration and back, and thereby perform a pincer-like motion. In the thermodynamically more stable cis isomer the lone pairs of the amino nitrogen atoms point towards each other, and in the trans form they point in opposite directions. The distance between the amino nitrogen atoms changes between 8 Å (cis) and 11 Å (trans isomer).

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20

Mckinnon, David M., Anthony S. Secco, and K. Ann Duncan. "The reaction of 2,1-benzisothiazoline-3-thiones with acetylenic reagents." Canadian Journal of Chemistry 65, no. 6 (June 1, 1987): 1247–53. http://dx.doi.org/10.1139/v87-211.

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N-Methyl-2,1-benzisothiazoline-3-thione reacts with acetylene esters to form o-iminobenzoquinone methides which either form diazocines 2 by head-to-tail dimerisation, or react further with the acetylenic ester forming diadducts. With phenylacetylene a 1,2-difhiolo[2,3-b]2,1-benzisofhiazole structure is obtained by rearrangement of an initial adduct. Related thiones and acetylenes react similarly but in poorer yields. The crystal and molecular structures of the diazocine were determined by single crystal X-ray diffractometry techniques. The compound crystallizes in space group [Formula: see text] with unit cell dimensions a = 7.9465(10), b = 13.6421(14), c = 13.9183(18) Å, α = 82.38(1), β = 83.67(1), γ = 85.77(1) deg, and Z = 2. The structure was solved by direct methods and refined to an R value of 0.056 for 3037 observed reflections. The structure consists of molecules of 2a which have an approximate C2 axis passing through the center of the eight-membered ring. Deviations from true symmetry result from internal ring strain, lone pair–lone pair repulsions, and packing effects.

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21

Löw, Roland, Talina Rusch, Fynn Röhricht, Olaf Magnussen, and Rainer Herges. "Diazocine-functionalized TATA platforms." Beilstein Journal of Organic Chemistry 15 (July 5, 2019): 1485–90. http://dx.doi.org/10.3762/bjoc.15.150.

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Recently, it has been shown that the thermochemical cis→trans isomerization of azobenzenes is accelerated by a factor of more than 1000 by electronic coupling to a gold surface via a conjugated system with 11 bonds and a distance of 14 Å. The corresponding molecular architecture consists of a platform (triazatriangulenium (TATA)) which adsorbs on the gold surface, with an acetylene spacer standing upright, like a post in the middle of the platform and the azobenzene unit mounted on top. The rate acceleration is due to a very peculiar thermal singlet–triplet–singlet mechanism mediated by bulk gold. To investigate this mechanism further and to examine scope and limitation of the “spin-switch catalysis” we now prepared analogous diazocine systems. Diazocines, in contrast to azobenzenes, are stable in the cis-configuration. Upon irradiation with light of 405 nm the cis-configuration isomerizes to the trans-form, which slowly returns back to the stable cis-isomer. To investigate the thermal trans→cis isomerization as a function of the conjugation to the metal surface, we connected the acetylene spacer in meta (weak conjugation) and in para (strong conjugation) position. Both isomers form ordered monolayers on Au(111) surfaces.

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22

Bieszczad, Bartosz, Damian Garbicz, Damian Trzybiński, Damian Mielecki, Krzysztof Woźniak, Elżbieta Grzesiuk, and Adam Mieczkowski. "Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design." Molecules 25, no. 4 (February 18, 2020): 906. http://dx.doi.org/10.3390/molecules25040906.

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A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

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23

Schnieders, Christoph, Walter Huber, Johann Lex, and Klaus Müllen. "1,5-Diazocine." Angewandte Chemie 97, no. 7 (July 1985): 579–80. http://dx.doi.org/10.1002/ange.19850970716.

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24

Bieszczad, Bartosz, Damian Garbicz, Damian Trzybiński, Marta K. Dudek, Krzysztof Woźniak, Elżbieta Grzesiuk, and Adam Mieczkowski. "Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design." Molecules 25, no. 12 (June 20, 2020): 2855. http://dx.doi.org/10.3390/molecules25122855.

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Unsymmetrically N-substituted and N,N’-disubstituted 5,12-dihydrodibenzo [b,f][1,4]diazocine-6,11-diones were synthesized in the new protocol. The desired modifications of the dibenzodiazocine scaffold were introduced at the stages of proper selection of building blocks as well as post-cyclization modifications with alkylation or acylation agents, expanding the structural diversity and possible applications of synthesized molecules. The extension of developed method resulted in the synthesis of novel: tricyclic 5,10-dihydrobenzo[b]thieno[3,4-f][1,4]diazocine-4,11-dione scaffold and fused pentacyclic framework possessing two benzodiazocine rings within its structure. Additionally, the unprecedented rearrangement of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones to 2-(2-aminophenyl)isoindoline-1,3-diones was observed under the basic conditions in the presence of sodium hydride for secondary dilactams. The structures of nine synthesized products have been established by single-crystal X-ray diffraction analysis. Detailed crystallographic analysis of the investigated tri- and pentacyclic systems has shed more light on their structural features. One cell line derived from non-cancerous cells (EUFA30—human fibroblasts) and three tumor cells (U87—human primary glioblastoma, HeLa—cervix adenocarcinoma, BICR18—laryngeal squamous cell carcinoma) were used to determine the cytotoxic effect of the newly synthesized compounds. Although these compounds showed a relatively weak cytotoxic effect, the framework obtained for 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione could serve as a convenient privilege structure for the design and development of novel bioactive molecules suitable for drug design, development and optimization programs.

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25

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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26

Eremeev, A. V., I. P. Piskunova, and R. S. �l'kinson. "New diazocine synthesis." Chemistry of Heterocyclic Compounds 21, no. 6 (June 1985): 707. http://dx.doi.org/10.1007/bf00515081.

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27

Preußke, Nils, Widukind Moormann, Katrin Bamberg, Matthias Lipfert, Rainer Herges, and Frank D. Sönnichsen. "Visible-light-driven photocontrol of the Trp-cage protein fold by a diazocine cross-linker." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2650–60. http://dx.doi.org/10.1039/c9ob02442e.

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28

Moormann, Widukind, Daniel Langbehn, and Rainer Herges. "Solvent-Free Synthesis of Diazocine." Synthesis 49, no. 15 (July 11, 2017): 3471–75. http://dx.doi.org/10.1055/s-0036-1590685.

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A convenient two-step synthesis of diazocine starting from 2-nitrotoluene is described. The first step, the oxidative dimerization of 2-nitrotoluene, is improved to 95% yield. The second step, the reductive azo cyclization, is performed as a solvent-free reaction with lead powder in a ball mill (51% yield). As a reference, the previously described azo cyclization with Zn/Ba(OH)2 is investigated in detail. The results explain why in previous experiments the yields are low and extremely dependent on the reaction conditions. In view of potential applications in photopharmacology, we checked the stability under reducing conditions. Diazocine does not react with glutathione, indicating intracellular stability.

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29

Zou, Yang, Jingyi Fei, Liangzhe Chen, Qingfeng Dong, and Houbin Li. "Application of Response Surface Methodology for Improving the Yield of 1,5-bis(ptoluenesulfonyl)- 3,7-Dihydroxyoctahydro-1,5-Diazocine." Current Organic Synthesis 16, no. 3 (June 17, 2019): 398–404. http://dx.doi.org/10.2174/1570179415666181113144357.

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Background: 3,3,7,7-tetrakis (difluoramino) octahydro-1,5-dinitro-1,5-diazocine (HNFX), as an important oxidizer in propellants, has received much attention due to its high density and energy. However, there are many difficulties that need to be solved, such as complex synthetic processes, low product yield, high cost of raw materials and complicated purification. In the synthesis of HNFX, the intermediate named 1,5-bis (p-toluenesulfonyl)-3,7-dihydroxyoctahydro-1, 5-diazocine (gem-diol), is difficult to synthesize. Methods: A simple method was used to synthesize the gem-diol. This prepared gem-diol was characterized by FT-IR, 1H NMR, melting point and mass spectrometry. In order to increase the yield of gem-diol, response surface methodology (RSM) was introduced to optimize experimental conditions. Results: After the establishment of the model, the optimal conditions of synthesis were found to be 9.33h for reaction time, 6.13wt. % for the concentration of NaOH and 1.38:1 for ratio of ECH (p-toluenesulfonamide): TCA (epichlorohydrin). Under the optimal conditions, the experimental value and the predicted value of yield were 22.18% and 22.92%, respectively. Conclusion: 1,5-bis (p-toluenesulfonyl)-3,7-dihydroxyoctahydro-1,5-diazocine (gem-diol) can be synthesized using the low cost of chemical materials, including p-toluenesulfonamide, epichlorohydrin, sodium hydroxide and ethanol. Response surface methodology (RSM) is an effective method to optimize the synthesis process, thereby improving the yield of gem-diol.

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30

Matheny, Jonathon P., Pavel M. Yamanushkin, Peter A. Petillo, and Michael Rubin. "Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes." RSC Advances 10, no. 72 (2020): 44183–90. http://dx.doi.org/10.1039/d0ra09014j.

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The sulfonamide moiety was evaluated as an activating and stabilizing functional group in the metal templated strain release-driven intramolecular nucleophilic addition of amines to cyclopropenes to generate 1,5-diazocan-2-ones.

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31

Schnieders, Christoph, Walter Huber, Johann Lex, and Klaus Müllen. "1,5-Diazocines." Angewandte Chemie International Edition in English 24, no. 7 (June 1985): 576–77. http://dx.doi.org/10.1002/anie.198505761.

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32

Moormann, Widukind, Daniel Langbehn, and Rainer Herges. "Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials." Beilstein Journal of Organic Chemistry 15 (March 20, 2019): 727–32. http://dx.doi.org/10.3762/bjoc.15.68.

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Seven symmetrically 3,3’-substituted diazocines were synthesized. Functional groups include alcohol, azide, amine and vinyl groups, which are suitable for polymer synthesis. Upon irradiation at 385 and 530 nm the diazocines perform a reversible, pincer-type movement switching the 3,3’-distance between 6.1 Å (cis, stable isomer) and 8.2 Å (trans, metastable isomer). Key reactions in the synthesis are an oxidative C–C coupling of 2-nitrotoluenes (75–82% yield) and a reductive ring closure to form the diazocines (56–60% yield). The cyclization of the dinitro compound to the azo compound was improved in yield and reproducibility, by over-reduction to the hydrazine and reoxidation to the azo unit. In contrast to 3,3’- and 4,4’-diaminodiazocine, which have been implemented in macromolecules for conformation switching, our compounds exhibit improved photophysical properties (photostationary states, separation of absorption bands in the cis and trans configuration). Hence they are promising candidates as molecular switches in photo and mechanoresponsive macromolecules and other smart materials.

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33

PERLMUTTER, H. D. "ChemInform Abstract: 1,2-Diazocines, 1,3-Diazocines, Triazocines, and Tetrazocines." ChemInform 22, no. 20 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199120313.

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34

Bhuiyan, M. Delower H., Paul Jensen, and Andrew C. Try. "2,8-Dimethoxy-4,10-dimethyl-1,3,7,9-tetranitro-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 24, 2007): o4393. http://dx.doi.org/10.1107/s1600536807050945.

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In the molecule of the title compound, C19H18N6O10, the 2,8-dimethoxy-4,10-dimethyl-1,3,7,9-tetranitro analogue of Tröger's base, the diazocine bridge imparts a twist such that the two aryl rings are offset with respect to one another. The hinge angle of the molecule, measured as the dihedral angle between the two benzene rings, is 103.64 (5)°.

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35

Cao, Wen-Bin, Bei-Bei Liu, Xiao-Ping Xu, and Shun-Jun Ji. "Cooperation of copper and dioxygen for the site-selective construction of benzo[1,5]diazocin-6(5H)-ones from indoles and enaminone analogues." Organic Chemistry Frontiers 5, no. 7 (2018): 1194–201. http://dx.doi.org/10.1039/c7qo01154g.

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36

Cho, S. K., J. H. Jung, Y. Sissembayeva, J. H. Song, D. I. Jung, and Y. H. Hwang. "Microwave Assisted Synthesis of Dibenzo-[b,f][1,5]diazocine Derivatives for Photocatalytic Water Splitting Applications." Asian Journal of Chemistry 33, no. 3 (2021): 627–31. http://dx.doi.org/10.14233/ajchem.2021.23056.

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Photocatalytic water splitting converts solar energy to storable hydrogen molecules which has the highest energy per mass. Most catalysts for photocatalytic water splitting utilize noble metals or precious metals. Organic photocatalysts are attracting more attention owing to several advantages like light weight, low cost, defined structure and tunability. In this study, the synthesis of several dibenzo[b,f][1,5]- diazocines via microwave irradiation for water splitting application is reported. Microwave irradiation facilitates fast, safe and simple synthesis in green reaction conditions. Mini library of dibenzo[b,f][1,5]diazocines were created in order to understand substituents effect on the photocatalytic activity.

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37

Sathyanarayana, Arruri, and Ganesan Prabusankar. "Facile access to imidazole and imidazolium substituted dibenzo-diazocines." New J. Chem. 38, no. 8 (2014): 3613–21. http://dx.doi.org/10.1039/c4nj00351a.

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Yogi, Seiichi, Kozo Hokama, and Otohiko Tsuge. "Novel Ring Contraction of 1,2-Diazocine System. Hydrolysis of 7-Substituted 4-Acetoxy- and 4-Phthalimido-3,8-diphenyl-1,2-diazocines Leading to the Formation of Pyrazoles." Chemistry Letters 16, no. 1 (January 5, 1987): 157–60. http://dx.doi.org/10.1246/cl.1987.157.

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39

Abe, Takumi, Koshiro Kida, and Koji Yamada. "A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines." Chemical Communications 53, no. 31 (2017): 4362–65. http://dx.doi.org/10.1039/c7cc01406f.

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Lentes, Pascal, Jeremy Rudtke, Thomas Griebenow, and Rainer Herges. "Substituted nitrogen-bridged diazocines." Beilstein Journal of Organic Chemistry 17 (June 25, 2021): 1503–8. http://dx.doi.org/10.3762/bjoc.17.107.

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Novel nitrogen-bridged diazocines (triazocines) were synthesized that carry a formyl or an acetyl group at the CH2NR-bridge and bromo- or iodo-substituents at the distant phenyl ring. The photophysical properties were investigated in acetonitrile and water. As compared to previous approaches the yields of the intramolecular azo cyclizations were increased (from ≈40 to 60%) using an oxidative approach starting from the corresponding aniline precursors. The Z→E photoconversion yields in acetonitrile are 80–85% and the thermal half-lives of the metastable E configurations are 31–74 min. Particularly, the high photoconversion yields (≈70%) of the water-soluble diazocines are noteworthy, which makes them promising candidates for applications in photopharmacology. The halogen substituents allow further functionalization via cross-coupling reactions.

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41

Tellkamp, Tobias, Jun Shen, Yoshio Okamoto, and Rainer Herges. "Diazocines on Molecular Platforms." European Journal of Organic Chemistry 2014, no. 25 (June 24, 2014): 5456–61. http://dx.doi.org/10.1002/ejoc.201402541.

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42

Kudo, Yoshiyuki, Teruyoshi Kimura, and Shuichi Hamada. "The Pyrolysis of 1,2,3,4,6,7-Hexathia-5,8-diazocine." Bulletin of the Chemical Society of Japan 63, no. 1 (January 1990): 235–40. http://dx.doi.org/10.1246/bcsj.63.235.

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Liu, Yanan, Zuwei Song, Libin Gao, and Jianzhong Li. "An Optical pH Sensor Based on Diazocine." ChemistrySelect 2, no. 26 (September 11, 2017): 7956–60. http://dx.doi.org/10.1002/slct.201700983.

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44

Ryu, Jaemin, Min-Jin Jo, Hyocheol Jung, Hayoon Lee, Donghee Shin, Miyeon Park, Kwang-Yol Kay, and Jongwook Park. "Synthesis and electroluminescent properties of diazocine derivatives." Molecular Crystals and Liquid Crystals 651, no. 1 (July 3, 2017): 77–84. http://dx.doi.org/10.1080/09273948.2017.1338890.

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45

Yang, Bingchuan, Guodong Shen, Xianqiang Huang, and Rutao Liu. "Design and Synthesis of a Novel Banana-Shaped Functional Molecule via Double Cross-Coupling." Molecules 24, no. 4 (February 15, 2019): 698. http://dx.doi.org/10.3390/molecules24040698.

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A novel banana-shaped molecule using 2,8-Dimethyl-6H,12H-5,11-methanodibenzo [b,f] [1,5]diazocine (Tröger’s base) as bent-core was synthesized via double Carbon-Carbon cross-coupling reaction. The double Sonogashira cross-coupling reaction was optimized by using Pd(PPh3)2Cl2 as catalyst, CuI as cocatalyst and diisopropylamine as base in place of triethylamine. The structure of this compound was confirmed by 1H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry.

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46

Faroughi, Masoud, Paul Jensen, and Andrew C. Try. "6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine." Acta Crystallographica Section E Structure Reports Online 63, no. 7 (June 8, 2007): o3111. http://dx.doi.org/10.1107/s160053680702661x.

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47

Faroughi, Masoud, Andrew C. Try, and Peter Turner. "6H,12H-5,11-Ethanodibenzo[b,f][1,5]diazocine." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (January 16, 2008): o458. http://dx.doi.org/10.1107/s1600536808000883.

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48

Kim, Taemin, Seokwoo Kang, Hyocheol Jung, Hayoon Lee, Donghee Shin, Miyeon Park, Kwang-Yol Kay, and Jongwook Park. "Synthesis and electroluminescent properties of new diazocine derivatives." Molecular Crystals and Liquid Crystals 662, no. 1 (February 11, 2018): 102–8. http://dx.doi.org/10.1080/15421406.2018.1466521.

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49

Wakamatsu, Hideaki, Yuichi Yoshimura, Yoshimi Sasaki, Masatoshi Kawahata, and Kentaro Yamaguchi. "Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides." Synthesis 50, no. 17 (May 30, 2018): 3467–86. http://dx.doi.org/10.1055/s-0037-1609857.

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Ring-closing metathesis (RCM) of ynamides, having alkene substituents of various lengths on the side chain, was demonstrated using the second-generation Grubbs catalyst. When the reaction of ene-ynamides was carried out in the presence of 5 mol% of the catalyst, RCM proceeded smoothly to give quinoline or isoquinoline derivatives having a dienamide unit in good yields. Furthermore, RCM of ene-ynamides, having one more carbon on the side chain, proceeded smoothly to provide seven-membered heterocycles having a dienamide component. Similarly, eight-membered heterocycles, diazocine and benzodiazocine, were also synthesized by RCM of ene-ynamides in good yields.

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Vande Velde, Christophe M. L., Benoît Tylleman, Matthias Zeller, and Sergey Sergeyev. "Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z′ for packing in the absence of strong crystal synthons." Acta Crystallographica Section B Structural Science 66, no. 4 (July 12, 2010): 472–81. http://dx.doi.org/10.1107/s0108768110021981.

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Crystal structures of Tröger's base (5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine) analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied. The incidence of Z′ > 1 structures increases to rather conspicuous levels. The reasons behind this trend are expanded upon, and a possible explanation is given in the flexibility of the alkyl substituents and van der Waals stabilization. In combination these effects allow for an additional stabilization of the packing by small changes in the molecular conformations, thus expanding the size of the asymmetric unit.

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