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Journal articles on the topic 'Dihydropyraziny'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Vlček, Pavel, Zdeněk Havlas, and Zdeněk Pavlíček. "Are 1,4-Dihydropyrazines Antiaromatic? Ab initio Study of 1,4-Dihydropyrazines and Their Tetrahydro Derivatives." Collection of Czechoslovak Chemical Communications 64, no. 4 (1999): 633–48. http://dx.doi.org/10.1135/cccc19990633.

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A set of twenty molecules containing 1,4-dihydro- or tetrahydropyrazine ring was calculated using ab initio methods. This set also includes previously prepared diacetyl- or disilyldihydropyrazines. Structures of 1,4-dihydropyrazine derivatives are strongly dependent on ring substituents and change from planar to heavily distorted boat conformations. In the planar and near-planar structures of some 1,4-diacyl- or 1,4-diformyl-1,4-dihydropyrazines, conjugation of nitrogen lone pairs and ring bond π electrons is small. Structures, bond lengths and bond orders of 1,4-dihydropyrazines and their tet

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2

Li, Huan Huan, Hai Bin Chu, Ying Nan Chen, et al. "Effects of Acidity on Nitrogen-Heterocyclic Compounds with Rare Earth Coordination and the Structure of Protonated Phenanthroline." Advanced Materials Research 233-235 (May 2011): 2808–11. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.2808.

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2,3-bis(2-pyridyl)-5,6-dihydropyrazine and a protonated phenanthroline (Phen) have been synthesized and the structure of protonated Phen is established by X-ray diffraction single crystal structure analysis. The coordination reactions of Phen, 2,2'- bipyridine and 2,3-bis(2-pyridyl)-5,6-dihydropyrazine with rare earth ions in low pH have been studied. The results show that 2,3-bis(2-pyridyl)-5,6-dihydropyrazine is hydrolyzed to be 2,2’-pyridil and protonated ethylenediamine. Meanwhile, Phen combines with proton, which results that nitrogen atoms can not coordinate with rare earth ions. The mol

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3

St. Hilaire, Valentine R., William E. Hopkins, Yenteeo S. Miller, Srinivasa R. Dandepally та Alfred L. Williams. "Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ5-2-oxopiperazines". Beilstein Journal of Organic Chemistry 15 (8 січня 2019): 72–78. http://dx.doi.org/10.3762/bjoc.15.8.

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The regioselective addition of Grignard reagents to mono- and disubstituted N-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45–100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ5-2-oxopiperazines providing a simple and efficient approach towards their preparation.

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4

Shoukat Ali, Shaikh Saddam, Kingshuk Roy, Naveenkumar Akula, Satishchandra B. Ogale, and Moumita Majumdar. "Air exposed 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine: an avant-garde carbonization precursor for multi-functionalized carbon material." Chemical Communications 56, no. 94 (2020): 14805–8. http://dx.doi.org/10.1039/d0cc06597h.

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5

Takechi, Shinji, Shigeru Ito, Nobuhiro Kashige, Takumi Ishida, and Tadatoshi Yamaguchi. "Glutathione depression by dihydropyrazine derivative." Journal of Toxicological Sciences 36, no. 2 (2011): 231–35. http://dx.doi.org/10.2131/jts.36.231.

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6

Takechi, Shinji, Shigeru Ito, Nobuhiro Kashige, Takumi Ishida, and Tadatoshi Yamaguchi. "Identification of dihydropyrazine-glutathione adducts." Journal of Toxicological Sciences 40, no. 4 (2015): 495–500. http://dx.doi.org/10.2131/jts.40.495.

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7

Gompper, Rudolf, and Walter Breitschaft. "Diazachinodimethane, donorsubstituierte Pyrazine und Dihydropyrazine." Angewandte Chemie 95, no. 9 (2006): 727–29. http://dx.doi.org/10.1002/ange.19830950908.

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8

Fan, Qiangwen, Xiaowei Duan, and Hong Yan. "Solid state [2 + 2] photocycloaddition for constructing dimers of N,N′-diacyl-1,4-dihydropyrazines based on thiourea-induced assembly." CrystEngComm 20, no. 8 (2018): 1151–57. http://dx.doi.org/10.1039/c7ce01996c.

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9

Rakhi, Ramachandran, and Cherumuttathu H. Suresh. "A DFT study on dihydropyrazine annulated linear polyacenes: aromaticity, stability and HOMO–LUMO energy modulation." Physical Chemistry Chemical Physics 18, no. 35 (2016): 24631–41. http://dx.doi.org/10.1039/c6cp03723b.

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Linear polyacene (LPA) mimics containing up to 34 rings have been designed by annulating dihydropyrazine units to LPA cores and they showed enhanced aromatic character than the LPA due to significant mixing of the N-lone pairs with the carbon π-orbitals.

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10

Molla, Gianluca, Marco Nardini, Paolo Motta, Paola D’Arrigo, Walter Panzeri, and Loredano Pollegioni. "Aminoacetone oxidase from Streptococcus oligofermentans belongs to a new three-domain family of bacterial flavoproteins." Biochemical Journal 464, no. 3 (2014): 387–99. http://dx.doi.org/10.1042/bj20140972.

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Determination of the 3D structure and biochemical characterization of aminoacetone oxidase from Streptomyces oligofermentans reveal that this enzyme belongs to a novel family of flavoproteins which catalyses the condensation of two aminoacetone molecules yielding 3,6-dimethyl-2,5-dihydropyrazine and, eventually, 2,5-dimethylpyrazine.

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11

Ueda, Yohei, Nagataka Tsujimoto, Taiga Yurino, Hayato Tsurugi, and Kazushi Mashima. "Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile via C–CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine." Chemical Science 10, no. 4 (2019): 994–99. http://dx.doi.org/10.1039/c8sc04437f.

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A catalyst system of [Ni(MeCN)<sub>6</sub>](BF<sub>4</sub>)<sub>2</sub>, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si–Me<sub>4</sub>-DHP) assisted cyanation of aryl halides in acetonitrile to give the corresponding aryl nitriles.

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12

Bera, Saurav, and Gautam Panda. "A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition." Org. Biomol. Chem. 12, no. 23 (2014): 3976–85. http://dx.doi.org/10.1039/c4ob00639a.

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Practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived intermediates is described.

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13

Moloudi, Maryam, Hassan Kabirifard, Sohila Piri, and Elham Naghizadeh. "Synthesis of 2,3-dicyanopyrazine and ethyl 5-amino-4,6-dicyanobiphenyl-3-carboxylate derivatives from ethyl aroylpyruvates." Heterocyclic Communications 24, no. 2 (2018): 99–102. http://dx.doi.org/10.1515/hc-2017-0190.

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AbstractReactions of ethyl 4-aryl-2,4-dioxobutanoates1a–cat ambient temperature with diaminomaleonitrile in glacial acetic acid and with malononitrile in ethanol/H2O (1:1) led to the formation of 5-(2-aryl-2-oxoethyl)-6-oxo-1,6-dihydropyrazine-2,3-dicarbontrile2a–cand ethyl 5-amino-4,6-dicyanobiphenyl-3-carboxylate derivatives3a–c, respectively.

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14

Strathausen, Rainer, Rainer Beckert, Jan Fleischhauer, Dirk Müller, and Helmar Görls. "Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes." Zeitschrift für Naturforschung B 69, no. 5 (2014): 641–49. http://dx.doi.org/10.5560/znb.2014-4002.

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The cycloacylation of oxalic amidines 7 with bis-imidoylchlorides 6 furnished the dihydropyrazine derivatives 8. Due to their vicinal amino-imino substructures, they provide good preconditions for a double intramolecular ring closure reaction. An alternative synthesis for hexaaza-pentacenes 1 was developed using potassium carbonate as the base and lead tetraacetate as the oxidizing agent.

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15

Sit, Sing-Yuen, Yazhong Huang, Ildiko Antal-Zimanyi, Sally Ward, and Graham S. Poindexter. "Novel Dihydropyrazine Analogues as NPY Antagonists." Bioorganic & Medicinal Chemistry Letters 12, no. 3 (2002): 337–40. http://dx.doi.org/10.1016/s0960-894x(01)00765-x.

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16

Takiguchi, Asahi, Mana Wakita, Satoru Hiroto, and Hiroshi Shinokubo. "Synthesis of Dihydropyrazine-fused Porphyrin Dimers." Chemistry Letters 48, no. 4 (2019): 371–73. http://dx.doi.org/10.1246/cl.190002.

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17

Anuradha, N., A. Thiruvalluvar, K. Pandiarajan, S. Chitra, and R. J. Butcher. "2-Methyl-3,5,6-triphenyl-2,3-dihydropyrazine." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (2009): o546. http://dx.doi.org/10.1107/s1600536809005042.

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18

Hemamalini, Madhukar, and Hoong-Kun Fun. "5,6-Di-2-thienyl-2,3-dihydropyrazine." Acta Crystallographica Section E Structure Reports Online 66, no. 5 (2010): o1062. http://dx.doi.org/10.1107/s1600536810012705.

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19

Wang, Yuanhao, Xiaoqiang Lei, and Yefeng Tang. "Rh(ii)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon." Chemical Communications 51, no. 21 (2015): 4507–10. http://dx.doi.org/10.1039/c5cc00268k.

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The Rh(ii)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-amino-pyrroles and 1,2-dihydropyrazines, respectively.

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20

Aly, Ashraf A., Alaa A. Hassan, Nasr K. Mohamed, et al. "Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones." Molecules 24, no. 20 (2019): 3782. http://dx.doi.org/10.3390/molecules24203782.

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Herein, we report the synthesis of 5,12-dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]-diquinoline-6,14(5H,12H)diones, 2-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-1,4-diphenyl- butane-1,4-diones and 4-(benzo-[d]oxazol-2-yl)-3-hydroxy-1H-[4,5]oxazolo[3,2-a]pyridine-1-one. The new candidates were synthesized and identified by different spectroscopic techniques, and X-ray crystallography.

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21

Brook, David J. R., Bruce C. Noll, and Tad H. Koch. "Dioxygen Oxidation of a Stable 1,4-Dihydropyrazine." Journal of Organic Chemistry 62, no. 20 (1997): 6767–72. http://dx.doi.org/10.1021/jo970222o.

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22

Takechi, Shinji, Kazuhide Nakahara, Masaru Adachi, and Tadatoshi Yamaguchi. "Oxidative Stress Induced by a Dihydropyrazine Derivative." Biological & Pharmaceutical Bulletin 32, no. 2 (2009): 186–89. http://dx.doi.org/10.1248/bpb.32.186.

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23

Pierra, Claire, Clément Counor, Richard Storer, and Gilles Gosselin. "Synthesis and antiviral evaluation of the 2′-C-methyl branched derivative of a nucleoside analog inhibitor of RNA viral infections, T-1106." Collection of Czechoslovak Chemical Communications 76, no. 11 (2011): 1327–33. http://dx.doi.org/10.1135/cccc2011089.

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An example of a 2′-C-methyl branched nucleoside analogue bearing 3,4-dihydro-3-oxopyrazine-2-carboxamide as the base, namely 4-(2-C-methyl-β-D-ribofuranosyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide, is reported. This compound was synthesized following a Vorbrüggen’s glycosylation procedure in a few steps. When evaluated in cell culture experiments against a broad range of viruses, this compound did not exhibit any significant antiviral effect or cytotoxicity.

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24

Handmann, Vera Iris, Markus Merget та Reinhold Tacke. "Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester". Zeitschrift für Naturforschung B 55, № 2 (2000): 133–38. http://dx.doi.org/10.1515/znb-2000-0201.

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Abstract In context with studies on silicon-containing α-amino acids and peptides, a strategy for the synthesis of the 4-sila-proline skeleton was developed. The synthesis of rac-and (R)-4,4-dimethyl-4-sila-proline ethyl ester [rac-2 and (R)-2] is described. Compounds rac-2 and (R)-2 (≥ 99% ee) were prepared by two-step syntheses, starting from 3,6-diethoxy-2,5-dihydro-pyrazine and (R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine, respectively.

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25

Schwedtmann, Kai, Jan Haberstroh, Sven Roediger, et al. "Formation of an imidazoliumyl-substituted [(LC)4P4]4+ tetracation and transition metal mediated fragmentation and insertion reaction (LC = NHC)." Chemical Science 10, no. 28 (2019): 6868–75. http://dx.doi.org/10.1039/c9sc01701a.

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Tetracationic cyclo-tetraphosphane [(L<sub>C</sub>)<sub>4</sub>P<sub>4</sub>]<sup>4+</sup> as triflate salt (L<sub>C</sub> = 4,5-dimethyl-1,3-diisopropyl-imidazol-2-yl) is obtained from the reduction of [L<sub>C</sub>PCl<sub>2</sub>]<sup>+</sup> with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine and represents the first salt of the cationic cyclo-phosphane series with the general formula [L<sub>n</sub>P<sub>n</sub>]<sup>n+</sup>.

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26

Yamaguchi, Tadatoshi, Shigeru Ito, Yukiko Iwase, Kenji Watanabe, and Kazunobu Harano. "A Diamine-Exchange Reaction of Dihydropyrazines." HETEROCYCLES 53, no. 8 (2000): 1677. http://dx.doi.org/10.3987/com-00-8932.

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27

Rodrigues, Anabela, Paula M. T. Ferreira, and Luís S. Monteiro. "Synthesis and reactivity of a 1,4-dihydropyrazine derivative." Tetrahedron 60, no. 38 (2004): 8489–96. http://dx.doi.org/10.1016/j.tet.2004.06.127.

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28

Takechi, Shinji, Kazuhide Nakahara, and Tadatoshi Yamaguchi. "Dihydropyrazine-Induced Inactivation of Glyceraldehyde-3-phosphate Dehydrogenase." Biological & Pharmaceutical Bulletin 33, no. 3 (2010): 379–83. http://dx.doi.org/10.1248/bpb.33.379.

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29

Sit, Sing-Yuen, Yazhong Huang, Ildiko Antal-Zimanyi, Sally Ward, and Graham S. Poindexter. "ChemInform Abstract: Novel Dihydropyrazine Analogues as NPY Antagonists." ChemInform 33, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.200225147.

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30

Stefańska, Anita, Tadeusz Ossowski, and Artur Sikorski. "2-(3-Chloro-1,2-dihydropyrazin-2-ylidene)malononitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (2009): o643. http://dx.doi.org/10.1107/s1600536809006783.

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31

Thiruvalluvar, A., N. Anuradha, S. Chitra, D. Devanathan, and R. J. Butcher. "2-Methyl-3-(4-methylphenyl)-5,6-diphenyl-2,3-dihydropyrazine." Acta Crystallographica Section E Structure Reports Online 68, no. 11 (2012): o3084. http://dx.doi.org/10.1107/s1600536812041438.

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32

Benecke, B., and M. Bolte. "trans- and cis-2,5-Dimethoxy-3,6-diphenyl-3,6-dihydropyrazine." Acta Crystallographica Section C Crystal Structure Communications 52, no. 10 (1996): 2586–88. http://dx.doi.org/10.1107/s0108270196006634.

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33

Anuradha, N., S. Chitra, A. Thiruvalluvar, et al. "2-(2-Chlorophenyl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine." Acta Crystallographica Section E Structure Reports Online 67, no. 10 (2011): o2598. http://dx.doi.org/10.1107/s1600536811036336.

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34

Nakahara, Kazuhide, Koki Yamaguchi, Yasuyuki Yoshitake, Tadatoshi Yamaguchi, and Kazunobu Harano. "Chemical Reactivity of Dihydropyrazine Derivatives. Cycloaddition Behavior toward Ketenes." CHEMICAL & PHARMACEUTICAL BULLETIN 57, no. 8 (2009): 846–52. http://dx.doi.org/10.1248/cpb.57.846.

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35

Tong, Chenhua, Wenguang Zhao, Jing Luo, et al. "Large-Size Linear and Star-Shaped Dihydropyrazine Fused Pyrazinacenes." Organic Letters 14, no. 2 (2012): 494–97. http://dx.doi.org/10.1021/ol2030839.

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36

Hossain, Asik, Santosh Pagire, and Oliver Reiser. "Visible-Light-Mediated Synthesis of Pyrazines from Vinyl Azides Utilizing a Photocascade Process." Synlett 28, no. 14 (2017): 1707–14. http://dx.doi.org/10.1055/s-0036-1590888.

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A convenient method for the synthesis of substituted pyrazines from vinyl azides has been developed. This method is enabled by a dual-energy and electron-transfer strategy by visible-light photocatalysis. Initially, vinyl azides are activated by a triplet sensitization process from an excited ruthenium photocatalyst in the presence of water to form dihydropyrazines, followed by a single-electron-transfer (SET) process under oxygen (air) atmosphere that leads to the tetrasubstituted pyrazines in good to excellent yields.

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37

Takechi, Shinji, Tadatoshi Yamaguchi, Hajime Nomura, et al. "Mutation Spectrum Induced by Dihydropyrazines in Escherichia coli." Biological & Pharmaceutical Bulletin 29, no. 1 (2006): 17–20. http://dx.doi.org/10.1248/bpb.29.17.

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38

Ito, Shigeru, Shinji Takechi, Kazuhide Nakahara, Nobuhiro Kashige, and Tadatoshi Yamaguchi. "Phenyl-Substituted Dihydropyrazines with DNA Strand-Breakage Activity." CHEMICAL & PHARMACEUTICAL BULLETIN 58, no. 6 (2010): 825–28. http://dx.doi.org/10.1248/cpb.58.825.

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39

Ito, Shigeru, Tomoya Hirano, Akiko Sugimoto, Hiroyuki Kagechika, Shinji Takechi, and Tadatoshi Yamaguchi. "Latent Enamine Functionality of 5-Methyl-2,3-dihydropyrazines." CHEMICAL & PHARMACEUTICAL BULLETIN 58, no. 7 (2010): 922–27. http://dx.doi.org/10.1248/cpb.58.922.

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40

Micheletti, Gabriele, Camilla Delpivo, and Carla Boga. "A Green Synthesis of Quinoxalines and 2,3-Dihydropyrazines." Synthesis 45, no. 11 (2013): 1546–52. http://dx.doi.org/10.1055/s-0033-1338441.

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41

Gopal, Damodaragounder, Dainius Macikenas, Lawrence M. Sayre, et al. "Structural Determination of a Dimeric Side-Product Accompanying Dihydropyrazine Preparation." Acta Chemica Scandinavica 51 (1997): 938–41. http://dx.doi.org/10.3891/acta.chem.scand.51-0938.

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42

Butler, Anthony R., and Elaine H. Brown. "Condensation of 2-hydroxy-2'-aminoacetophenone to form a dihydropyrazine." Arkivoc 2002, no. 3 (2002): 166–71. http://dx.doi.org/10.3998/ark.5550190.0003.318.

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43

Lemp, Else, Antonio L. Zanocco, German Günther, and Nancy Pizarro. "Solvent Effect on the Sensitized Photooxygenation of 2,3-Dihydropyrazine Derivatives." Journal of Organic Chemistry 68, no. 8 (2003): 3009–16. http://dx.doi.org/10.1021/jo026303o.

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44

Skubnevskaya, G. I., L. B. Volodarskii, and A. Ya Tikhonov. "2,2,5,5-Tetramethyl-2,5-dihydropyrazine 1,4-dioxide ?A new spin trap." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 5 (1985): 1102–4. http://dx.doi.org/10.1007/bf01142814.

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45

Gollnick, Klaus, and Sigrid Koegler. "Photosensitized oxygenation of 2,3-dihydropyrazines: Unexpected synthesis of isonitriles." Tetrahedron Letters 29, no. 10 (1988): 1127–30. http://dx.doi.org/10.1016/s0040-4039(00)86667-8.

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46

Chorvat, Robert J., and Kurt J. Rorig. "Synthesis of 4-aryl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyrazines." Journal of Organic Chemistry 53, no. 24 (1988): 5779–81. http://dx.doi.org/10.1021/jo00259a033.

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47

Kashige, Nobuhiro, Toru Takeuchi, Shigenobu Matsumoto, Shinji Takechi, Fumio Miake, and Tadatoshi Yamaguchi. "Radical Species in DNA Strand-Cleavage Caused by Dihydropyrazines." Biological & Pharmaceutical Bulletin 28, no. 3 (2005): 419–23. http://dx.doi.org/10.1248/bpb.28.419.

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48

Maruoka, Hiroshi, Nobuhiro Kashige, Fumio Miake, and Tadatoshi Yamaguchi. "Synthesis of New Dihydropyrazines with DNA Strand-Breakage Activity." CHEMICAL & PHARMACEUTICAL BULLETIN 53, no. 10 (2005): 1359–61. http://dx.doi.org/10.1248/cpb.53.1359.

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49

Nakahara, Kazuhide, Shinji Takechi, Koki Yamaguchi, Kazunobu Harano, and Tadatoshi Yamaguchi. "Tetraazaindenes Derived from Dihydropyrazines with DNA Strand-Breaking Activity." CHEMICAL & PHARMACEUTICAL BULLETIN 57, no. 12 (2009): 1371–75. http://dx.doi.org/10.1248/cpb.57.1371.

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50

Brook, David J. R., Bruce C. Noll, and Tad H. Koch. "Carbonyl and thiocarbonyl stabilized 1,4-dihydropyrazines: synthesis and characterization." Journal of the Chemical Society, Perkin Transactions 1, no. 2 (1998): 289–92. http://dx.doi.org/10.1039/a705391f.

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