Skip to main content
SpringerLink
Log in

Fluorinated Triazines

  • Chapter
  • First Online:
Fluorine in Heterocyclic Chemistry Volume 2

Abstract

In this chapter data on structure, synthetic routes, reactivity of derivatives of 1,2,3-triazines, 1,2,4-triazines and 1,3,5-triazines − bearing one or several fluorine atoms in heterocyclic ring as well as trifluoromethyl substituted triazines are considered and analyzed, and also their certain representatives are discussed. The bibliography – 119 references.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Boggs J, Pang F (1984) The structural effects of fluorine substitution in pyridine, pyrimidine, and s-triazine: an Ab initio study. J Heterocycl Chem 21:1801–1805

    Article  CAS  Google Scholar 

  2. Schleyer P, Buzek P, Klapotke T, Tornieporth-Oetting I, Broschag M, Pickardt J (1993) Preparation of 1-fluoro-2,4,6-trihalogeno-s-triazinium hexafluoroarsenates: structure of [C3N3Cl3F][AsF6] as deduced by experimental and ab initio methods. Inorg Chem 32:1523–1524

    Article  CAS  Google Scholar 

  3. McMurran J, Kouvetakis J, Nesting D (1998) Synthesis of molecular precursors to carbon−nitrogen−phosphorus polymeric systems. Chem Mater 10:590–593

    Article  Google Scholar 

  4. Kingston M, Chen S, Lork E, Mews R (2004) Anionic triazine systems. J Chem Soc Dalton Trans 2004:1400–1404

    Article  Google Scholar 

  5. Todd M, Kouvetakis J, Groy T (1995) Novel synthetic routes to carbon nitride. Chem Mater 7:1422–1426

    Article  CAS  Google Scholar 

  6. Burger H, Koplin R, Pawelke G (1983) Reaction of perfluorotrimethylamine with antimony pentafluoride. Synthesis and X-ray structure of perfluorinated hexahydro-triazinedione derivative. J Fluor Chem 22:175–183

    Article  Google Scholar 

  7. Nikolaeva S, Kolbin A, Sapozhnikov Y, Valitov R, Ivanov V (1990) Synthesis of fluoro-substituted symmetrical dialkylaminotriazines under interphase-catalysis conditions. Chem Heterocycl Compd 26:1142–1144

    Article  Google Scholar 

  8. Chambers R, Korn S, Sandford G (1992) Polyhalogenoheterocyclic compounds. Part 40. Tertiary aromatic amines as carbon-nucleophiles with activated perfluorinated aromatic compounds. Tetrahedron 48:7939–7950

    Article  CAS  Google Scholar 

  9. Mallah E, Kuhn N, Maichle-Moβmer C, Steimann M, Ströbele M, Zeller K (2009) Nucleophilic aromatic substitution with 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene. Zteitschrift Naturforsch 64b:1176–1182

    Google Scholar 

  10. Brewer S, Burnell H, Holden I, Jones B, Willis C (1999) Synthesis of a series of dichloroamino- and dihalosulfonamido-1,3,5-triazines and investigation of their hindered rotation and stereodynamic behaviour by NMR spectroscopy. J Chem Soc Perkin Trans 2:1231–1234

    Article  Google Scholar 

  11. Chambers R, Shepherd T, Tamura M (1988) Polyhalogenoheterocyclic compounds – 38: synthesis of trifluoro-1,2,3-triazine and perfluoro-isopropyl derivatives. Tetrahedron 44:2583–2590

    Article  CAS  Google Scholar 

  12. Barlow M, Haszeldine R, Simon C (1980) Heterocyclic polyfluoro-compounds. Part 30. Perfluoroalkylation of trifluoro-1,2,4-triazine. J Chem Soc Perkin Trans 1 1980:2254–2257

    Google Scholar 

  13. Nosova E, Lipunova G, Charushin V, Chupakhin O (2011) Ftorsoderzhaschie azini i benzazini [Fluorinated azines and benzazines]. Publishing of Ural Branch of Russian Academy of Sciences, Ekaterinburg

    Google Scholar 

  14. Breidung J, Burger H, McNaught D, Senzlober M, Thiel W (1999) Ab initio and high resolution infrared study of FC ≡ CBr. Spectrochim Acta 55A:695–708

    Article  CAS  Google Scholar 

  15. Chambers R, Tamura M, Howard J, Johnson O (1987) Perfluoroalkyl-1,2,3-triazines: novel nucleophilic attack on ring nitrogen. J Chem Soc Chem Commun 22:1697–1698

    Article  Google Scholar 

  16. Ulomsky E, Medvedeva N, Schepochkin A, El’tsov O, Rusinov V, Chupakhin O, Deeva E, Kiselyov O (2011) Fluorinated [1,2,4]triazolo[1,5-a]pyrimidines and [1,2,4]triazolo[5,1-c][1,2,4]triazines. Chem Heterocycl Compd 47:1411–1417

    Google Scholar 

  17. Farkas J (1983) Synthesis of 1,2,4-triazine-3,5(2H,4H)-diones containing electronegative substituents in position 6. Collect Czechoslov Chem Commun 48:2676–2681

    Article  CAS  Google Scholar 

  18. Koenig J, Schenherr M, Wolter P, Maja C (1984) Über die Fluorierung von 6-Azauracil und seinem Ribosid. Zteitschrift Chem 24:253–254

    CAS  Google Scholar 

  19. Durr G (1967) 1,3-dimethyl-5-fluoro-6-azauracil and some 5-bromo-6-azauracil derivatives. J Med Chem 10:288–289

    Article  CAS  Google Scholar 

  20. Barlow M, Haszeldine R, Simon C, Simpkin D, Ziervogel G (1982) Heterocyclic polyfluoro-compounds. Part 39. Preparation and some nucleophilic substitution reactions of trifluoro-1,2,4-triazine. J Chem Soc Perkin Trans 1:1251–1254

    Article  Google Scholar 

  21. Rykowski A, Plas H (1980) Ring transformations and amination in reactions of 3-halo-5-phenyl-1,2,4-triazines with potassium amide in liquid ammonia. J Org Chem 45:881–885

    Article  CAS  Google Scholar 

  22. Jovanovic M (1985) Fluoroheterocycles II. Synthesis of 3-fluro-1,2,4-triazine 2-oxides. Heterocycles 23:1969–1981

    Article  CAS  Google Scholar 

  23. Haenel F, John R, Seitz G (1989) Trifluormethyl-substituierte, heterocyclisch anellierte Pyridine durch intramolekulare Diels-Alder-Cycloaddition mit inversem Elektronenbedar. Arch Pharm 325:349–352

    Article  Google Scholar 

  24. John R, Seitz G (1989) 3-methylthio-5-trifluormethyl-1,2,4-triazin als Edukt zur Synthese heteroanellierter Pyridine durch intramolekulare Diels-Alder-Cycloaddition mit inversem Elektronenbedarf. Arch Pharm 322:561–564

    Article  CAS  Google Scholar 

  25. Russel M, Carling R, Street L, Hallett D, Goodacre S, Mezzogori E, Reader M, Cook S, Bromidge F, Newman R, Smith A, Wafford K, Marshall G, Reynolds D, Dias R, Ferris P, Stanley J, Lincoln R, Tye S, Sheppard W, Sohal B, Pike A, Dominguez M, Atack J, Castro J (2006) Discovery of imidazo[1,2-b][1,2,4]triazines as GABAA α2/3 subtype selective agonists for the treatment of anxiety. J Med Chem 49:1235–1238

    Article  Google Scholar 

  26. Kamitori Y, Hojo M, Masuda R, Sukegawa M, Hayashi K, Kouzeki K (1994) A convenient and facile synthesis of 5-trifluoromethyl-1,2,4-triazine derivatives. Heterocycles 39:155–162

    Article  CAS  Google Scholar 

  27. Honey M, Pasceri R, Lewis W, Moody C (2012) Diverse trifluoromethyl heterocycles from a single precursor. J Org Chem 77:1396–1405

    Article  CAS  Google Scholar 

  28. Katagiri N, Watanabe H, Kaneko C (1988) Cyclocondensations in synthesis. XXXVII. Synthesis of 6-trifluoromethyl-1,2,4-triazines and -1,2,4-triazin-5-ones and their pericyclic reactions with olefins. Chem Pharm Bull 36:3354–3372

    Article  CAS  Google Scholar 

  29. Dipple A, Heidelberger C (1966) Fluorinated pyrimidines. XXVIII. The synthesis of 5-trifluoromethyl-6-azauracil and 5-trifluoromethyl-6-aza-2′-deoxyuridine. J Med Chem 9:715–718

    Article  CAS  Google Scholar 

  30. Richter M, Seitz G (1995) Synthese des ersten 1,2,4-Triazin-C-Nukleosids und dessen Umwandlung in neue Pyridin-C-Nukleoside durch “inverse” [4 + 2]-Cycloaddition. Arch Pharm 328:175–180

    Article  CAS  Google Scholar 

  31. Seitz G, Siegl J (1997) Synthesis of novel pyridine-C-nucleosides of 2,3-dideoxyribose by “inverse” <4 + 2 > -cycloaddition. Z Naturforschung 52B:851–858

    Google Scholar 

  32. Seitz G, Lachmann J (1999) Synthese neuer Pyridin-, Pyrindin- bzw. Isochinolin-substituierter α- und β-C-Nukleoside der 2-Desoxy-D-ribose. Z Naturforschung 54B:549–558

    Google Scholar 

  33. Che D, Siegl J, Seitz G (1999) Synthesis of chiral 2-(2′-pyrrolidinyl)pyridines from (S)- and (R)-proline: potential ligands of the neuronal nicotinic acetylcholine receptors. Tetrahedron Asymmetry 10:573–585

    Article  CAS  Google Scholar 

  34. Seitz G, Mohr R (1986) Elektronenreiche C=N-doppelbindungen als heterodienophile gegenüber 3,6-bis(trifluormethyl)-1,2,4,5-tetrazin. Arch Pharm 319:690–694

    Article  CAS  Google Scholar 

  35. Biermann U, Glemser O, Knaak J (1967) Über Reaktionen von Stickstofftrifluorid und Tetrafluorhydrazin mit verschiedenen CN-Verbindungen. Chem Ber 100:3789–3794

    Article  CAS  Google Scholar 

  36. Emeleus H, Hurst G (1964) 70. Fluorination of cyanogen and cyanogen chloride with metal fluorides. J Chem Soc 1964:396–399

    Google Scholar 

  37. Dresdner R, Tlumac F, Young J (1960) Fluorocarbon nitrogen compounds. V. Nitrogen trifluoride as a reagent in fluorocarbon chemistry. J Am Chem Soc 82:5831–5834

    Article  CAS  Google Scholar 

  38. Fawcett F, Lipscomb R (1964) Cyanogen fluoride: synthesis and properties. J Am Chem Soc 86:2576–2579

    Article  CAS  Google Scholar 

  39. Athanassios T, Bruno C (2002) Reactive disazo dyes, their production and their use. ЕP Patent 1207186, 22 May 2002

    Google Scholar 

  40. Fernandezcid M, Van Spronsen J, Van der Kraan M, Veugelers W, Woerlee G, Witkamp G (2007) A significant approach to dye cotton in supercritical carbon dioxide with fluorotriazine reactive dyes. J Supercrit Fluids 40:477–484

    Article  CAS  Google Scholar 

  41. Banks R, Barlow M, Mamaghani M (1981) On the synthesis and properties of hydrazinium(1+) fluoride. J Fluor Chem 17:197–203

    Article  CAS  Google Scholar 

  42. Hynes J, Bishop B, Bandyopadhyay P, Bigelow L (1963) The action of elementary fluorine upon organic compounds. XXVI. The direct fluorination of some perfluoroalkyl-s-triazines. J Am Chem Soc 85:83–86

    Article  CAS  Google Scholar 

  43. Mitsch R (1965) Organic fluoronitrogens. II. The reductive defluorination reaction. J Am Chem Soc 87:328–333

    Article  CAS  Google Scholar 

  44. Kirchmeier R, Sprenger G, Shreeve J (1975) (CF2NCl)3, a new mild fluorinating reagent. Inorg Nucl Chem Lett 11:699–703

    Article  CAS  Google Scholar 

  45. Maxwell A, Fry J, Bigelow L (1958) The indirect fluorination of cyanuric chloride. J Am Chem Soc 80:548–549

    Article  CAS  Google Scholar 

  46. Grisley D, Gluesenkamp J, Heininger S (1958) Reactions of nucleophilic reagents with cyanuric fluoride and cyanuric chloride. J Org Chem 23:1802–1804

    Article  CAS  Google Scholar 

  47. Fawcett F, Lipscomb R (1959) Triazines. XXII. Fluoro-s-triazines. J Am Chem Soc 81:3769–3770

    Article  Google Scholar 

  48. Tullock C, Carboni R, Harder R, Smith W, Coffman D (1960) The chemistry of sulfur tetrafluoride. VII. Synthesis of organic fluorides by halogen exchange with sulfur tetrafluoride. J Am Chem Soc 82:5107–5110

    Article  CAS  Google Scholar 

  49. Kober E, Schroeder H, Ratz R, Ulrich H, Grundmann C (1962) Synthesis of polyfluorinated heterocycles by indirect fluorination with silver fluorides. I. Fluoro-s-triazines and reactions of cyanuric fluoride. J Org Chem 27:2577–2580

    Article  Google Scholar 

  50. Englin M, Makarov S, Dubov S, Yakubovich A (1965) Fluorination of cyanuric acid derivatives. Zhurnal Obshchei Khimii 35:1416–1420

    CAS  Google Scholar 

  51. Franz R (1980) Ueber trishydrofluoride tertiaerer amine und ihren einsatz als fluorierungsmittel. J Fluor Chem 15:423–434

    Article  CAS  Google Scholar 

  52. Hitzke J (1981) Les fluorations comparees des chloropyrimidines et de la chloro-s-triazine en milieu de fluorure de potassiun solide. J Fluor Chem 17:385–401

    Article  CAS  Google Scholar 

  53. Murray C, Sandford G, Korn S (2003) Ionic liquids as media for nucleophilic fluorination. J Fluor Chem 123:81–84

    Article  CAS  Google Scholar 

  54. Groß S, Laabs S, Scherrmann A, Sudau A, Zhang N, Nubbemeyer U (2000) Improved syntheses of cyanuric fluoride and carboxylic acid fluorides. J für praktische Chemie 342:711–714

    Article  Google Scholar 

  55. Shaw G, Seaton D, Bissell E (1961) Fluorine-containing nitrogen compounds. IV. Hexafluoro-1,3,5-trichloro-1,3,5-triazacyclohexane. J Org Chem 26:4765–4767

    Article  CAS  Google Scholar 

  56. Tullock C, Coffman D (1960) Synthesis of fluorides by metathesis with sodium fluoride. J Org Chem 25:2016–2019

    Article  CAS  Google Scholar 

  57. Yoneda N, Fukuhara T (1996) Facile preparation of aromatic fluorides by deaminative fluorination of aminoarenes using hydrogen fluoride combined with bases. Tetrahedron 52:23–36

    Article  CAS  Google Scholar 

  58. Norris W, Merwin L, Ostrom G (1997) Formation of urea, isourea, and triazine derivatives from diisopropylcyanamide with trifluoroacetic anhydride and trifluoromethanesulfonic anhydride: thermal instability of urea and isourea derivatives. J Org Chem 62:9070–9075

    Article  CAS  Google Scholar 

  59. Shmel’kova T, Ignatenko A, Krukovskii S, Ponomarenko V (1989) Synthesis of fluoro-containing substituted 1,3,5-triazines. Bull Acad Sci USSR Div Chem Sci 38:836–840

    Article  Google Scholar 

  60. Schafer B (1999) A ZnCl2-catalysed synthesis of 2-amino-4-trifluoromethyl-6-methoxy-1,3,5-triazine. Synth Commun 29:475–479

    Article  CAS  Google Scholar 

  61. Dao P, Garbay C, Chen H (2012) High yielding microwave-assisted synthesis of tri-substituted 1,3,5-triazines using Pd-catalyzed aryl and heteroarylamination. Tetrahedron 68:3856–3860

    Article  CAS  Google Scholar 

  62. Norton T (1950) A new synthesis of ethyl trifluoroacetate. J Am Chem Soc 72:3527–3528

    Article  CAS  Google Scholar 

  63. Reilly W, Brown H (1957) Reactions of the perfluoronitriles. II. Syntheses of 2,4,6-tris(perfluoroalkyl)-1,3,5-triazines. J Org Chem 22:698–700

    Article  CAS  Google Scholar 

  64. Yang Z (2003) Preparation of highly fluorinated cyclopropanes and ring-opening reactions with halogens. J Org Chem 68:4410–4416

    Article  CAS  Google Scholar 

  65. Young J, Dressler R (1967) Fluorocarbon nitrogen compounds. XI. Functionally active perfluoroalkyl-substituted s-triazines. J Org Chem 32:2237–2241

    Article  CAS  Google Scholar 

  66. Kelarev V, Remizov A, Karakhanov R, Polivin Y, Oietaio D (1992) Synthesis and properties of sym-triazines. 10 synthesis of 2,4-diamino-sym-triazines containing a sterically hindered phenol substituent. Chem Heterocycl Compd 28:1189–1193

    Article  Google Scholar 

  67. Koshelev V, Kelarev V, Karakhanov R, Shalkarov S (1995) Synthesis of N-substituted 2,4-diamino-1,3,5-triazines containing pyridyl groups. Russ J Org Chem 31:260–263

    Google Scholar 

  68. Alkalay D, Volk J, Bartlett M (1976) Conversion of biguanides into substituted s-triazines assayable by GC or mass fragmentography. J Pharm Sci 65:525–529

    Article  CAS  Google Scholar 

  69. Buu-Hoï N, Jacquignon P, Mangane M, Béranger S, Pinhas H (1972) Synthesis, properties, and electron impact fragmentation of fluorinated 1-arylbiguanides. J Chem Soc Perkin Trans 1:278–282

    Article  Google Scholar 

  70. Shaw J, Gross F (1959) The preparation of certain amino-substituted perfluoroalkyl-s-triazines. J Org Chem 24:1809–1811

    Article  CAS  Google Scholar 

  71. Shapiro S, Parrino V, Freedman L (1960) Guanamines. III. Perfluoroalkylguanamines and related compounds. J Org Chem 25:379–384

    Article  CAS  Google Scholar 

  72. Cockburn W, Bannard R (1957) The reaction of acetic and trifluoroacetic anhydrides with some substituted guanidine hydrochlorides. Can J Chem 35:1285–1292

    Article  CAS  Google Scholar 

  73. Chen H, Dao P, Laporte A, Garbay C (2010) High yielding microwave-assisted synthesis of 2-(arylmethyl)amino-4-arylamino-6-alkyl-1,3,5-triazines. Tetrahedron Lett 51:3174–3176

    Article  CAS  Google Scholar 

  74. Okajima N, Okada Y (1991) Synthesis and reaction of 2-amino-1m3-thiazetidines and 2-imino-1,3-dithietanes. J Heterocycl Chem 28:177–185

    Article  CAS  Google Scholar 

  75. Groll M, Wunderlich K (1981) Reactive dyestuffs. US Patent 4267107, 12 May 1981

    Google Scholar 

  76. Ehrig V, Groll M, Wunderlich K (1981) Phthalocyanine reactive dyestuffs, their preparation and their use for dyeing materials containing hydroxyl groups or amide groups. US Patent 4286962, 1 Sept 1981

    Google Scholar 

  77. Harms W, Kuth R, Wunderlich K (1985) Halogenotriazinyl dyestuffs. US Patent 4503224, 5 Mar 1985

    Google Scholar 

  78. Chambers R, Tamura M (1985) Fluorinated 1,2,3-triazines. J Fluor Chem 29:127

    Article  Google Scholar 

  79. Seitz G, John R (1989) Zur Reaktivität von Cyanamiden gegenüber akzeptorsubstituierten 1,2,4-Triazinen. Chem Ber 122:1381–1383

    Article  CAS  Google Scholar 

  80. John R, Seitz G (1990) Synthese von Sieben- und Achtring-anellierten Pyridinen durch “inverse” intramolekulare Diels-Alder-Reaktion mit Trifluormethyl-substituierten 1,2,4-Triazinen. Chem Ber 123:133–136

    Article  CAS  Google Scholar 

  81. Chambers R, Korn S, Sandford G (1994) Reactions involving fluoride ion. Part 37. ‘Proton Sponge’ hydrofluoride as a fluoride ion donor. J Fluor Chem 69:103–108

    Article  CAS  Google Scholar 

  82. Chambers R, Gray W, Korn S (1995) Reactions involving fluoride ion. Part 40. Amines as initiators of fluoride ion catalysed reactions. Tetrahedron 51:13167–13176

    Article  CAS  Google Scholar 

  83. Chambers R, Magron C, Howard J, Yufit D (1999) Reactions involving fluoride ion. Part 45. An approach to surface treatment using perfluoro-(isopropyl)-s-triazines. J Fluor Chem 97:69–74

    Article  CAS  Google Scholar 

  84. Novák V, Dobáš I (1976) Basicity of symmetrical 2-substituted 4,6-diaminotriazines. Collect Czech Chem Commun 41:3378–3383

    Article  Google Scholar 

  85. Lork E, Chen SJ, Kniter G, Mews R (1994) Fluoride ion attack towards triazines. Phosphorus Sulfur Silicon 94:309–311

    Article  Google Scholar 

  86. Hain J, Trpp J, Krasnova L, Sharpless K, Fokin V (2009) Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angew Chem Int Edit 48:8018–8021

    Article  Google Scholar 

  87. Olah G, Fung A, Gupta B, Narang S (1980) Synthetic methods and reactions; 80. Deoxygenation of sulfoxides with cyanuric chloride and fluoride. Synthesis 221–221

    Google Scholar 

  88. Huchel U, Schmidt C, Schmidt R (1998) Synthesis of hetaryl glycosides and their glycosyl donor properties. Eur J Org Chem 1998:1353–1360

    Article  Google Scholar 

  89. Chen Y, Wang D, Huang Z, Wang M (2010) Synthesis, structure, and functionalization of homo heterocalix[2]arene[2]triazines: versatile conformation and cavity structures regulated by the bridging elements. J Org Chem 75:3786–3796

    Article  CAS  Google Scholar 

  90. Otten JW, Otten HU, Nee R, Meininger F (1982) Process for the manufacture of dihalogenotriazinylamino-naphthol compounds. US Patent 4361698, 30 Nov 1982

    Google Scholar 

  91. Bentley TW, Ratecliff J, Renfrew A, Taylor J (1996) Rate–product correlations for concurrent nucleophilic displacements of halotriazines by hydroxide and alkoxides in water. J Chem Soc Perkin Trans 2:2377–2381

    Article  Google Scholar 

  92. Zotou A, Eleftheriadis I, Heli M, Pegiadou S (2002) Ion-pair high performance liquid chromatographic study of the hydrolysis behaviour of reactive fluorotriazinic dyes. Dyes Pigments 53:267–275

    Article  CAS  Google Scholar 

  93. Cid M, Van Spronsen J, Van der Kraan M, Veugelers W, Woerlee G, Witkamp G (2005) Excellent dye fixation on cotton dyed in supercritical carbon dioxide using fluorotriazine reactive dyes. Green Chem 7:609–615

    Article  Google Scholar 

  94. Xie K, Song G, Hou A, Liu Y (2006) Mathematical model of reaction for reactive dyes containing fluorotriazine. Int J Nonlinear Sci Numer Simul 7:117–119

    CAS  Google Scholar 

  95. Krasnova L, Hein J, Fokin V (2010) Synthesis of 7-aza-5-deazapurine analogues via copper(I)-catalyzed hydroamination of alkynes and 1-iodoalkynes. J Org Chem 75:8662–8665

    Article  CAS  Google Scholar 

  96. Karygiannis G, Athanassopoulos C, Mamos P, Karamanos N, Papaionnou D, Francic GW (1998) Preparation and properties of enantiomerically pure Nα-tritylamino acid fluorides. Acta Chem Scand 52:1144–1150

    Article  CAS  Google Scholar 

  97. Kzuya K, Nobuhiro K, Kohtaro T, Akira T, Aiko O, Hitoshi K (1999) Novel 1,3,5-triazine derivatives with herbicidal activity. Pestic Sci 55:642–645

    Article  Google Scholar 

  98. Hynesb J, Bishop I, Bandyopadhyay P, Bigelow L (1963) The action of elementary fluorine upon organic compounds. Fluorination of some perfluoroalkyl-s-triazines. J Am Chem Soc 85:83–86

    Article  Google Scholar 

  99. Kobayashi Y, Ohsawa A, Honda M (1973) Studies on organic fluorine compounds. XII. Photolis of (fluoroalkyl)-s-triazines. Chem Pharm Bull 21:1575–1582

    Article  CAS  Google Scholar 

  100. Kobayashi Y, Kumadaki I, Hanzawa Y, Mimura M (1975) Studies on organic fluorine compounds. XVIII. On the mechanism of the conversion of trifluoromethyl group to amino group on a quinoline ring. Chem Pharm Bull 23:2044–2047

    Article  CAS  Google Scholar 

  101. Shaw J (1962) The preparation of s-triazine derivatives containing the N–O bond. I. Mono-N-oxides of amino-substituted s-triazine derivatives. J Org Chem 27:3890–3896

    Article  CAS  Google Scholar 

  102. Cho A, Kim C, Ray A, Zhang L (2011) 1′-Substituted carba-nucleozide products for antiviral treatment. WO Patent 150288, 1 Dec 2011

    Google Scholar 

  103. Cho S, Yoon J, Myung S, Chung K, Ho L (2003) Triazinylaninlino-disazo dyes, methods of preparing them and their use for dyeing and printing fiber materials. EP Patent 1367099, 3 Dec 2003

    Google Scholar 

  104. Lehmann U, Tzikas A, Frick M (2001) Black-dyeing inks and their use. EP Patent 1149135, 31 Oct 2001

    Google Scholar 

  105. Enrenberg S, Worner J, Livesey T (2005) Reactive azo dyes, their preparation and their use. US Patent 2005/159592, 21 July 2005

    Google Scholar 

  106. Gorlitz G, Russ W (2006) Water-soluble fiber reactive dyes, their preparation and their use. US Patent 2006/213016, 28 Sept 2006

    Google Scholar 

  107. Sire J, Tzikas A, Roentgen G (2007) Mixtures of reactive dyes and their use in a method for trichromatic dyeing or printing. WO Patent 2007/62958, 7 June 2007

    Google Scholar 

  108. Muller B (2007) Fibre-reactive anthraquinone dyes, process for their preparation and the use thereof. US Patent 2007/151049, 5 July 2007

    Google Scholar 

  109. Reichert H, Verdugo T (2007) Reactive dyes, a process for their preparation and their use. WO Patent 2007/77129, 12 July 2007

    Google Scholar 

  110. Tzikas A, Klier H, Roentgen G (2011) Fibre-reactive azo dyes, their preparation and their use. WO Patent 2011/18274, 17 Feb 2011

    Google Scholar 

  111. Christnacher H, Tzikas A, Roentgen G (2010) Reactive dyes, their preparation and their use. US Patent 7887602, 24 June 2010

    Google Scholar 

  112. Harms W, Wunderlich K, Oertzen K (1989) One-amine-2-sulpho-4-[(4-halo-6-aminotriazinyl-2)aminocyclohexylamino]anthraquinone reactive dyestuffs. US Patent 4837320, 6 June 1989

    Google Scholar 

  113. Jarman M, Coley H, Judson I, Thornton T, Wilman D, Abel G, Rutty C (1993) Synthesis and cytotoxicity of potential tumor-inhibitory analogs of trimelamol (2,4,6-tris[(hydroxymethyl)methylamino]-1,3,5-triazine) having electron-withdrawing groups in place of methyl. J Med Chem 36:4195–4200

    Article  CAS  Google Scholar 

  114. Millward S, Henning R, Kwong G, Pitram S, Agnew H, Deyle K, Nag A, Hein J, Lee SS, Lim J, Pfeilsticker J, Sharpless K, Heath J (2011) Iterative in situ click chemistry assembles a branched capture agent and allosteric inhibitor for Akt1. J Am Chem Soc 133:18280–18288

    Article  CAS  Google Scholar 

  115. Mattson R, Denhart D, Catt J, Dee M, Deskus J, Ditta J, Epperson J, King H, Gao A, Poss M, Purandare A, Tortolani D, Zhao Y, Yang H, Yeola S, Palmer J, Torrente J, Stark A, Johnson G (2004) Aminotriazine 5-HT7 antagonists. Bioorg Med Chem Lett 14:4245–4248

    Article  CAS  Google Scholar 

  116. Fujino H, Goya S (1990) A fluorogenic reagent: 3-(4,6-difluorotriazinyl)amino-7-methoxycoumarin, for the determination of amantadine by high-performance liquid chromatography. Chem Pharm Bull 38:544–545

    Article  CAS  Google Scholar 

  117. Fujino H, Goya S (1989) 3-(Difluoro-1,3,5-triazinyl)-1-(ethylthio)-2-n-propyl-benz[f]isoindole as a fluorescence derivatization reagent for estrogens in high-performance liquid chromatography. Chem Pharm Bull 37:1939–1940

    Article  CAS  Google Scholar 

  118. Ghiggino K, Hutchison J, Langford S, Latter M, Takezaki M (2006) Triaminotriazines-photophysical investigations of a porphyrin-appended triazine receptor with a naphthalene diimide guest. J Phys Org Chem 19:491–494

    Article  CAS  Google Scholar 

  119. Croft T, Zollinger J (1974) Perfluoroalkyl ether Di-s-triatinyl substituted alkanes. Ind Eng Chern Prod Res Dev 13:144–147

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University named after the First President of Russia Boris N. Yeltsin, Ekaterinburg, Russia

    Vladimir L. Rusinov & Emiliya V. Nosova

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia

    Valery N. Charushin

Authors
  1. Vladimir L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Emiliya V. Nosova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Valery N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vladimir L. Rusinov .

Editor information

Editors and Affiliations

  1. Department of Chemistry, Moscow State University, Moscow, Russia

    Valentine Nenajdenko

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Rusinov, V.L., Nosova, E.V., Charushin, V.N. (2014). Fluorinated Triazines. In: Nenajdenko, V. (eds) Fluorine in Heterocyclic Chemistry Volume 2. Springer, Cham. https://doi.org/10.1007/978-3-319-04435-4_8

Download citation

Publish with us

Policies and ethics

Search

Navigation