Login Register Cart 0
Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

The Chemistry of Triazine Isomers: Structures, Reactions, Synthesis and Applications

Author(s): Neelottama Kushwaha* and C.S. Sharma

Volume 20, Issue 20, 2020

Page: [2104 - 2122] Pages: 19

DOI: 10.2174/1389557520666200729160720

Price: $65

Abstract

Triazine is the six-membered heterocyclic ring containing three nitrogens, which replace the carbon-hydrogen unit in the benzene ring. Based on nitrogen position present in the ring system, it is categorized in three isomeric forms, i.e., 1, 2, 3-triazine (vicinal triazine), 1, 2, 4-triazine (asymmetrical triazine or isotriazine) and 1, 3, 5-triazine (symmetrical or s-triazine or cyanidine). Triazines have a weakly basic property. Their isomers have much weaker resonance energy than benzene structure, so nucleophilic substitution reactions are more preferred than electrophilic substitution reactions. Triazine isomers and their derivatives are known to play important roles possessing various activities in medicinal and agricultural fields such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal, antimalarial and antimicrobial agents.

Keywords: Heterocyclic, triazines, chemical reactivity, triazine synthesis, potent, biological activity.

« Previous Next »
Graphical Abstract

[1]
Yang, R.; Kaplan, P.A. Reaction of isothiourea with 2, 3-diaza-3- pentenedioic anhydride: A solid-phase synthesis of 3-amino-1, 2, 4-triazin-5(4H)-ones. Tetrahedron Lett., 2001, 42, 4433-4435.
[http://dx.doi.org/10.1016/S0040-4039(01)00766-3]
[2]
Hirai, K.; Sugimoto, H.; Mizushima, T.J. Triazinone derivative and antitumor agent JP: 61134389 A2, 1986.
[3]
Oettmeier, W.; Hilp, U.; Draber, W.; Fedtke, C.; Schmidt, R.R. Structure-activity relationships of triazinone herbicides on resistant weeds and resistant chlamydomonas reinhardtii. Pesticidal Society, 1991, 33, 399-409.
[http://dx.doi.org/10.1002/ps.2780330402]
[4]
Kranz, E.; Santel, H.; Luerssen, K. New 6-cyclo-butyl-1, 2, 4-triazinone derivs—useful as herbicides and plant growth regulators DE: 3917043 A1 1990.
[5]
Migawa, M.T.; Drach, J.C.; Townsend, L.B. Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-methyl-1-(beta-D-ribofuranosyl)- and 3-amino-5-methyl-1-(2-deoxy-beta-D-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaazaacenaphthylene as analogues of triciribine. J. Med. Chem., 2005, 48(11), 3840-3851.
[http://dx.doi.org/10.1021/jm0402014 ] [PMID: 15916436]
[6]
Rosowsky, A.; Forsch, R.A.; Moran, R.G.N. -[4-[[(3,4-dihydro-4-oxo-1,2,3-benzotriazin-6- yl)methyl]amino]benzoyl]-L-glutamic acid, a novel A-ring analogue of 2-desamino-5,8-dideazafolic acid. J. Med. Chem., 1992, 35(14), 2626-2630.
[http://dx.doi.org/10.1021/jm00092a013 ] [PMID: 1635061]
[7]
Garutia, L.; Roberti, M.; Rossi, T.; Castelli, M.; Malagoli, M. Synthesis and antiproliferative activity of 3-substituted 1H-indole [3, 2-d] 1, 2, 3-triazin-4 (3H)-ones. Eur. J. Med. Chem., 1998, 33, 43-46.
[http://dx.doi.org/10.1016/S0223-5234(99)80074-9]
[8]
Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Heterocyclic synthesis. Chem. Pharm. Bull. (Tokyo), 1982, 30, 3994-3999.
[http://dx.doi.org/10.1248/cpb.30.3994]
[9]
Cascioferro, S.; Parrino, B.; Spano, V.; Caobone, A.; Montalbano, A.; Barraja, P.; Diana, P.; Cirrincione, G. Synthesis and antitumor activities of 1,2,3-triazine and their benzo and heterofused derivatives. Eur. J. Med. Chem., 2017, 142, 1-13.
[http://dx.doi.org/10.1016/j.ejmech.2017.06.003]
[10]
Zhao, X.W.; Liu, D.; Luan, S.L.; Hu, G.D.; Lv, J.L.; Jing, Y.K.; Zhao, L.X. Synthesis and biological evaluation of 1,2,3-benzotrizene and pyrido [3,2-d]-1,2,3-triazine as inhibitor of vascular endothelial growth factor receptor-2. Bioorg. Med. Chem., 2013, 21, 7807-7815.
[http://dx.doi.org/10.1016/j.bmc.2013.10.009 ] [PMID: 24189187]
[11]
Kumar, R.; Singh, A.D.; Singh, J.; Singh, H.; Roy, R.K.; Chaudhary, A. 1,2,3-Triazine scaffold as a potent biologically active moiety: a mini review. Mini Rev. Med. Chem., 2014, 14(1), 72-83.
[http://dx.doi.org/10.2174/1389557513666140103111017 ] [PMID: 24387709]
[12]
Zvarych, V.; Stasevych, M.; Novikov, V.; Rusanov, E.; Vovk, M.; Szweda, P.; Grecka, K.; Milewski, S. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New class of antistaphylococcal agents: Synthesis and biological evaluation. Molecules, 2019, 24(24), 4581-4600.
[http://dx.doi.org/10.3390/molecules24244581] [PMID: 31847306]
[13]
Hamama, W.S.; El-Bana, G.G.; Shaaban, S.; Habib, O.M.O.; Zoorob, H.H. Advances in the domain of 4-amino-3-mercapto- 1,2,4-triazine-5-ones. RSC Advances, 2016, 6, 24010-24049.
[http://dx.doi.org/10.1039/C5RA26433B]
[14]
Abdel-Rahman, R.M.; Morsy, J.M.; Hanafy, F.; Amene, H.A. Synthesis of heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anticancer drugs: Part I. Pharmazie, 1999, 54(5), 347-351.
[PMID: 10368828]
[15]
Abdel-Rahman, R.M.; Morsy, J.M.; el-Edfawy, S.; Amine, H.A. Synthesis of some new heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anti-cancer drugs, Part II. Pharmazie, 1999, 54(9), 667-671.
[PMID: 10522270]
[16]
Heilman, W.P.; Heilman, R.D.; Scozzie, J.A.; Wayner, R.J.; Gullo, J.M.; Ariyan, Z.S. Synthesis and antihypertensive activity of novel 3-hydrazino-5-phenyl-1,2,4-triazines. J. Med. Chem., 1979, 22(6), 671-677.
[http://dx.doi.org/10.1021/jm00192a012 ] [PMID: 458822]
[17]
Topliss, J.G. Some observations on classical QSAR. Perspect. Drug Discov. Des., 1993, 1, 253-268.
[http://dx.doi.org/10.1007/BF02174527]
[18]
Ambhore, A.N.; Surywanshi, V.D.; Kamble, R.D.; Shrikant, V.H.; Mogle, P.P.; Kadam, S.S.; Dawane, B.S. Synthesis and biological investigation of isoxazolo[4,5-e][1,2,4]triazine derivatives. Pharma Chem., 2015, 7, 278-283.
[19]
Baumann, M.; Baxendale, I.R. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles. Beilstein J. Org. Chem., 2013, 9, 2265-2319.
[http://dx.doi.org/10.3762/bjoc.9.265 ] [PMID: 24204439]
[20]
Qiang, Z.; Yu, W.; Yu, Y. Design and development of novel 1,3,5-Triazine-Procaine derivatives as Protective agent against Myocardial ischemia/ Reperfusion injury via inhibitor of Nuclear factor-KB. Pharmacology, 2019, 104(3-4), 126-138.
[http://dx.doi.org/10.1159/000500702 ] [PMID: 31212291]
[21]
Rao, D.S.; Kumar, G.V.P.; Pooja, B.; Harika, G.; Kumar, Y.A.; Rao, G.S. An extensive review on 1,2,3 and 1,2,4-triazines scaffold-valuable lead molecules with potent and diverse pharmacological activities. Der Chemica Sinica, 2016, 7, 101-130.
[22]
Fiorot, R.G.; Westphal, R.; Lemos, B.C.; Romagna, R.A.; Gonclaves, P.L.; Fernandes, M.R.N.; Ferriera, C.V.; Taranto, A.G.; Greco, S.J. Synthesis, Molecular Modelling and Anticancer activities of new molecular hybrids containing 1,4- Naphthoquinone, 7-Chloroquinoline, 1,3,5- Triazine and morpholine cores as P13K and AMPK inhibitors in the metastatic melanoma cells. J. Braz. Chem. Soc., 2019, 0, 1-14.
[http://dx.doi.org/10.21577/0103-5053.20190096]
[23]
Kar, A. Medicinal Chemistry, 5th ed; New age international publishers: New Delhi, 2010.
[24]
Stukov, A.N.; Korsakov, M.V.; Khrapova, T.N.; Kil’maeva, N.E.; Kraĭz, B.O. Effect of dioxadet on tumors transplanted to the brain. Vopr. Onkol., 1986, 32(10), 64-67.
[PMID: 3776129]
[25]
Stukov, A.N.; Filov, V.A.; Kon’kov, S.A.; Ivin, B.A. The pharmacological properties of preparations from the aziridinyl triazine group. Eksp. Klin. Farmakol., 1996, 59(1), 58-60.
[PMID: 8704637]
[26]
Bespalov, V.G.; Beliaeva, O.A.; Panchenko, A.V.; Stukov, A.N.; Gershanovich, M.L.; Murazov, IaG.; Kon’kov, S.A.; Kil’maeva, N.E.; Krylova, I.M.; Mironiuk, T.A.; Latipova, D.Kh. Antitumor activity of dioxadet compared with cisplatin on ascitic ovarian tumor in rats. Vopr. Onkol., 2011, 57(6), 771-774.
[PMID: 22416396]
[27]
Tripathi, K.D. Essentials of medical pharmacologyJaypee brothers medical publishers (P) Ltd: New Delhi, , 2003.
[28]
Arya, K.; Dandia, A. Synthesis and cytotoxic activity of trisubstituted-1,3,5-triazines. Bioorg. Med. Chem. Lett., 2007, 17(12), 3298-3304.
[http://dx.doi.org/10.1016/j.bmcl.2007.04.007 ] [PMID: 17449247]
[29]
Zheng, M.; Xu, C.; Ma, J.; Sun, Y.; Du, F.; Liu, H.; Lin, L.; Li, C.; Ding, J.; Chen, K.; Jiang, H. Synthesis and antitumor evaluation of a novel series of triaminotriazine derivatives. Bioorg. Med. Chem., 2007, 15(4), 1815-1827.
[http://dx.doi.org/10.1016/j.bmc.2006.11.028 ] [PMID: 17157510]
[30]
Menicagli, R.; Samaritani, S.; Signore, G.; Vaglini, F.; Dalla Via, L. In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: New molecules in anticancer research. J. Med. Chem., 2004, 47(19), 4649-4652.
[http://dx.doi.org/10.1021/jm0495374 ] [PMID: 15341480]
[31]
Kumar, R.; Gupta, L.; Pal, P.; Khan, S.; Singh, N.; Katiyar, S.B.; Meena, S.; Sarkar, J.; Sinha, S.; Kanaujiya, J.K.; Lochab, S.; Trivedi, A.K.; Chauhan, P.M.S. Synthesis and cytotoxicity evaluation of (tetrahydro-beta-carboline)-1,3,5-triazine hybrids as anticancer agents. Eur. J. Med. Chem., 2010, 45(6), 2265-2276.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.001 ] [PMID: 20207053]
[32]
Kondaparla, S.; Debnath, U.; Soni, A.; Dola, V.R.; Sinha, M.; Srivastava, K.; Puri, S.K.; Katti, S.B. Synthesis, biological evaluation and molecular modeling studies of chiral chloroquine analogues as antimalarial agents. Antimicrob. Agents Chemother., 2018, 62(12), e02347-17.
[http://dx.doi.org/10.1128/AAC.02347-17 ] [PMID: 30224532]
[33]
Greif, G. Triazinone compounds for treating diseases resulting from infestation with parasitic protozoans US Patent, 20090181040 2009.
[34]
Stock, M.L.; Elazab, S.T.; Hsu, W.H. Review of triazine antiprotozoal drugs used in veterinary medicine J. Vet. Pharmacol. Therap, 2017, 1-11.
[35]
Agarwal, A.; Srivastava, K.; Puri, S.K.; Chauhan, P.M. Syntheses of 2,4,6-trisubstituted triazines as antimalarial agents. Bioorg. Med. Chem. Lett., 2005, 15(3), 531-533.
[http://dx.doi.org/10.1016/j.bmcl.2004.11.052 ] [PMID: 15664807]
[36]
Katiyar, S.B.; Srivastava, K.; Puri, S.K.; Chauhan, P.M. Synthesis of 2-[3,5-substituted pyrazol-1-yl]-4,6-trisubstituted triazine derivatives as antimalarial agents. Bioorg. Med. Chem. Lett., 2005, 15(22), 4957-4960.
[http://dx.doi.org/10.1016/j.bmcl.2005.08.023 ] [PMID: 16168643]
[37]
Bhat, H.R.; Singh, U.P.; Gahtori, P.; Ghosh, S.K.; Gogoi, K.; Prakash, A.; Singh, R.K. Synthesis, docking, in vitro and in vivo antimalarial activity of hybrid 4-aminoquinoline-1,3,5-triazine derivatives against wild and mutant malaria parasites. Chem. Biol. Drug Des., 2015, 86(3), 265-271.
[http://dx.doi.org/10.1111/cbdd.12490 ] [PMID: 25487527]
[38]
Bhat, H.R.; Singh, U.P.; Thakur, A.; Ghosh, S.K.; Gogoi, K.; Prakash, A.; Singh, R.K. Synthesis, antimalarial activity and molecular docking of hybrid 4-aminoquinoline-1,3,5-triazine derivatives. Experiment. Parasitol., 2015, 157, 59-67.
[39]
Bhat, H.R.; Singh, U.P.; Yadav, P.S.; Kumar, V.; Gahtori, P.; Das, A.; Chetia, D.; Prakash, A.; Mahanta, J. Synthesis, characterization and antimalarial activity of hybrid 4-aminoquinoline-1,3,5-triazine derivatives. Arab. J. Chem., 2016, 9, S625-S631.
[http://dx.doi.org/10.1016/j.arabjc.2011.07.001]
[40]
Klimova, E.I.; Klimova, T.; Alamo, M.F.; Iturbide, D.M.; Garcia, M.M. Synthesis, structure and some chemical properties of Diferrocenyl-1,2,3-triazine. Heterocyclic Chem., 2009, 46, 477-483.
[http://dx.doi.org/10.1002/jhet.93]
[41]
Adger, B.M.; Bradbury, S.; Keating, M.; Charles, W.R.; Storr, R.C.; Williams, M.T. 1,2,3-Benzotriazines. J. Chem. Soc., Perkin Trans. 1, 1975, 31-40.
[http://dx.doi.org/10.1039/p19750000031]
[42]
Zhao, X.W.; Liu, D.; Luan, S.L.; Hu, G.D.; Lv, J.L.; Jing, Y.K.; Zhao, L.X. Synthesis and biological evaluation of substituted 1,2,3-benzotriazines and pyrido[3,2-d]-1,2,3-triazines as inhibitors of vascular endothelial growth factor receptor-2. Bioorg. Med. Chem., 2013, 21(24), 7807-7815.
[http://dx.doi.org/10.1016/j.bmc.2013.10.009 ] [PMID: 24189187]
[43]
Stevens, H.N.E.; Stevens, M.F.G. Triazines and related products., Part III. Synthesis and rearrangement of 3,4-dihydro-4-imino-1,2,3-benzotriazines J. Chem. Soc C: Organic 1970, 765-771.
[44]
Paudler, W.W.; Chen, T.K. 1, 2, 4-triazine. III.A Conveninent synthesis of 1, 2, 4-triazine and their covalent hydration. J. Heterocycl. Chem., 1970, 7, 767-771.
[http://dx.doi.org/10.1002/jhet.5570070403]
[45]
Phucho, I.T.; Nongpiur, A.; Tumtin, S; Nongrum, R.; Myrboh, B.; Nongkhlaw, R.L. Novel one pot synthesis of substituted 1, 2, 4-triazines Archive for organic chemistry 2008, 79-87.
[46]
Neunhoeffer, H.; Wiley, P.F. Chemistry of 1 2 3-Triazines and 1 2 4-Triazines, trazines, and Pentazin 1978.
[47]
Elks, J.; Ganellin, C.R. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and bibliographies, edi. First Sringerscience+business media, B.V, 1990.
[48]
Tang, S.; He, J.; Sun, Y.; He, L.; She, X. Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles. Org. Lett., 2009, 11(17), 3982-3985.
[http://dx.doi.org/10.1021/ol901626n ] [PMID: 19708706]
[49]
Hughes, R.A.; Thompson, S.P.; Alcaraz, L.; Moody, C.J. Total synthesis of the thiopeptide antibiotic amythiamicin D. J. Am. Chem. Soc., 2005, 127(44), 15644-15651.
[http://dx.doi.org/10.1021/ja0547937 ] [PMID: 16262432]
[50]
Sangshetti, J.N.; Shinde, D.B. One pot synthesis and SAR of some novel 3-substituted 5,6-diphenyl-1,2,4-triazines as antifungal agents. Bioorg. Med. Chem. Lett., 2010, 20(2), 742-745.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.048 ] [PMID: 20005098]
[51]
Kaila, J.C.; Baraiya, A.B.; Pandya, A.N.; Jalani, H.B.; Sudarsanam, V.; Vasu, K.K. A convenient one-pot synthesis of trisubstituted 1, 3, 5-triazines through intermediary amidinothioureas. Tetrahedron Lett., 2010, 51, 1486-1489.
[http://dx.doi.org/10.1016/j.tetlet.2010.01.034]
[52]
Biswas, S.; Batra, S. One- Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes. Eur. J. Org. Chem., 2012, 2012, 3492-3499.
[http://dx.doi.org/10.1002/ejoc.201200276]
[53]
Mundy, B.P.; Ellerd, M.G.; Favaloro, F.G. Name Reactions and Reagents in Organic Synthesis, A john wiley & sons, inc., publication, edi; Second, 2005.
[http://dx.doi.org/10.1002/9780471739876]
[54]
Laue, T.; Plagens, A. Named. Organic. Reactions., 2005.
[55]
Simsons, J.K.; Saxton, M.R. Working with Hazardous Chemicals: Benzoguanamine. Org. Synth., 1953, 33, 13.
[http://dx.doi.org/10.15227/orgsyn.033.0013]
[56]
Seifer, G.B. Cyanuric Acid and Cyanurates. Russ. J. Coord. Chem., 2002, 28, 301.
[http://dx.doi.org/10.1023/A:1015531315785]
[57]
Baldaniya, B.B.; Patel, P.K. Synthesis, Antibacterial and Antifungal Activities of s-Triazine Derivatives. E-J. Chem., 2009, 6, 673-680.
[http://dx.doi.org/10.1155/2009/196309]
[58]
Harris, R.L.N. Synthesis of Triazines from N-Cyanocarbamimidates Synthesis, 1981, 1981, 907-908.
[59]
Baldaniya, B.B. Synthesis and Characterizations of N 2 -(Aryl)-N 4, N 6 - bis (6, 7-dichloro-1, 3-benzothiazol-2-yl)-1, 3, 5- triazine-2, 4, 6-triamines as Biological Potent Agents. E-J. Chem., 2010, 7, 210-214.
[http://dx.doi.org/10.1155/2010/612853]
[60]
Campbell, J.J.A.; Noyce, S.J.; Storr, R.C. The reaction of 1, 2, 3-benzotriazines with Grignard reagents. J. Chem. Soc. Chem. Commun., 1983, 1344-1346.
[http://dx.doi.org/10.1039/c39830001344]
[61]
Koyama, J.; Toyokuni, I.; Tagahara, T. Diels-Alder Reaction of 1, 2, 3-Benztriazine with Enamine: Application to the synthesis of Alkaloids, 2-Propylquinoline and 2- Phenylquinoline. Chem. Pharm. Bull. (Tokyo), 1998, 46, 332-334.
[http://dx.doi.org/10.1248/cpb.46.332]
[62]
Koyama, J.; Toyokuni, I.; Tagahara, T. Synthesis of 2-Arylquinoline and 2-Aryl-4-quinoline alkaloid via Diels-Alder reaction of 1, 2, 3-Benzotriazine with enamines. Chem. Pharm. Bull. (Tokyo), 1999, 47, 1038-1039.
[http://dx.doi.org/10.1248/cpb.47.1038]
[63]
Boulton, A.J.; Kiss, M.; Saka, J.D.K. 1, 2, 3-Benzotriazine 2-oxides. J. Chem. Soc. Perkin. Trans., 1988, I, 1509-1512.
[http://dx.doi.org/10.1039/p19880001509]
[64]
Atkinson, C.M.; Cossey, H.D. 305. Quaternisation of some 1, 2, 4-triazines. J. Chem. Soc., 1963, 1628-1635.
[http://dx.doi.org/10.1039/jr9630001628]
[65]
Boger, D.L.; Panek, J.S. Diels-Alder reaction of heterocyclic azadienes. I. Thermal cycloaddition of 1, 2, 4-triazine with enamines: simple preparation of substituted pyridines. J. Org. Chem., 1981, 46, 2179-2182.
[http://dx.doi.org/10.1021/jo00323a044]
[66]
Mieczyslawmakosza., Tow-Phase reaction in organic chemistry Survey of progress in chemistry, 1980, 9, 1-53.
[67]
Catozzi, N.; Edwards, M.G.; Raw, S.A.; Wasnaire, P.; Taylor, R.J.K. Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach. J. Org. Chem., 2009, 74(21), 8343-8354.
[http://dx.doi.org/10.1021/jo901761r ] [PMID: 19780559]
[68]
Konno, S.; Ohba, S.; Sagi, M.; Yamanaka, H. Studies on as-Triazine derivatives IX. Synthesis of 5-Substituted 1,2,4-Triazine derivatives through an addition reaction and substituent oxidation. Chem. Pharm. Bull. (Tokyo), 1987, 35, 1378-1382.
[http://dx.doi.org/10.1248/cpb.35.1378]
[69]
Metze, R.; Scherowsky, G. Über 1.2.4-Triazine, X.; Über die Hydrierung von 1.2.4-Triazinen. Chem. Ber., 1959, 92, 2481-2486.
[http://dx.doi.org/10.1002/cber.19590921014]
[70]
Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, The Chemistry of Heterocycles, 2nd ed; Wiley-VCH Verlag, 2003.
[http://dx.doi.org/10.1002/352760183X]
[71]
Setsuya, O.; Shoetsu, K.; Hiroshi, Y. Studies on as Triazine Derivatives. XVI. Reaction of 1,2,4-Triazinecarbonitriles with carbanions. Chem. Pharm. Bull. (Tokyo), 1991, 39, 486-488.
[http://dx.doi.org/10.1248/cpb.39.486]
[72]
Setsuya, O.; Mataichi, S.; Etsuko, T.; Satoshi, F.; Kazuhiko, H.; Hiroshi, Y. Synthesis of alkenyl-1, 2, 4-triazine derivatives. Chem. Pharm. Bull. (Tokyo), 1988, 36, 1721-1726.
[http://dx.doi.org/10.1248/cpb.36.1721]
[73]
Grundmann, C. Syntheses with s-Triazine. Angew. Chem. Int. Ed. Engl., 1963, 2, 309-323.
[http://dx.doi.org/10.1002/anie.196303091]
[74]
Lozinskii, M.O.; Chenko, A.Y. Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine. Chem. Heterocycl. Compd., 2009, 45, 376-399 [Review].
[http://dx.doi.org/10.1007/s10593-009-0294-7]
[75]
Kreutzberger, A. Cyanamid als NH-aktive komponate in der synthese von dehydro-N-mannich basen. Tetrahedron, 1972, 28, 4877-4880.
[http://dx.doi.org/10.1016/0040-4020(72)88095-5]
[76]
Kreutzberger, A. Gattermannsche Aldehydsynthese mit s-Triazin statt Blausaure. Angew. Chem., 1967, 79, 978.
[http://dx.doi.org/10.1002/ange.19670792204]
[77]
Aksenov, A.V.; Aksenova, I.V. Use of the ring opening reactions of 1, 3, 5-triazines in organic synthesis. Chem. Heterocycl. Compd., 2009, 45, 130-150 [review].
[http://dx.doi.org/10.1007/s10593-009-0243-5]
[78]
Bohme, R.M.; Dang, Q. 1, 3, 5-Triazine 2008.
[79]
Jha, H.C.; Zilliken, F.; Breitmaier, E. Isoflavone Synthesis with 1, 3, 5-Triazine. Angew. Chem. Int. Ed. Engl., 1981, 20, 102-103.
[http://dx.doi.org/10.1002/anie.198101021]
[80]
Kreutzberger, A.; Stevens, M.F.G. Aminomethinylation of aromatic amines. J. Chem. Soc. C, 1969, 9, 1282-1285.
[http://dx.doi.org/10.1039/j39690001282]
[81]
Kaminski, Z.J.; Paneth, P.; Rudzinski, J. A study on the activation of carboxylic acids by means of 2-Cloro-4,6-Dimethoxy-1,3,5-trizine and 2-Cloro-4,6-diphenoxy-1,3,5-triazine. J. Org. Chem., 1998, 63, 4248-4255.
[http://dx.doi.org/10.1021/jo972020y]

Rights & Permissions Print Cite
Article Metrics
51
1
© 2024 Bentham Science Publishers | Privacy Policy