Synthesis 2002(7): 0901-0905
DOI: 10.1055/s-2002-28512
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Fluorine Containing Triazolo- and Tetrazolopyrimidines

Arcady L. Krasovsky, Andrew M. Moiseev, Valentine G. Nenajdenko*, Elizabeth S. Balenkova
Department of Chemistry, Moscow State University, 119899 Moscow, Russia
Fax: +7(095)9328846; e-Mail: Nen@acylium.chem.msu.su;
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Publikationsverlauf

Received 5 February 2002
Publikationsdatum:
14. Mai 2002 (online)

Abstract

The reaction of 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b with corresponding aminoazoles was investigated. A new simple and efficient way for the regioselective synthesis of 5-CF3 or 7-CF3 triazolo- and tetrazolopyrimidines is described.

    References

  • 1a Filler R. In Fluorine Containing Drugs in Organofluorine Chemicals and Their Industrial Applications   Pergammon; New York: 1979.  Chapter 6.
  • 1b Holland GF. Pereira JN. J. Med. Chem.  1967,  10:  149 
  • 2a Rempfler H, and Duerr D. inventors; EP  337944.  ; Chem. Abstr. 1990, 112, 139043r
  • 2b Rempfler H, Duerr D, and Thummel RC. inventors; EP  337943.  ; Chem. Abstr. 1990, 112, 139044s
  • 3a Heidelberg C. Annu. Rev. Pharmacol. Toxicol.  1967,  7:  10 
  • 3b Duschinsky R. Pleven E. Heidelberg C. J. Am. Chem. Soc  1957,  79:  4559 
  • 3c Hillers S, Lazdins A, Veinbergs K, and Sidorov B. inventors; US Patent  4039546.  ; Chem. Abstr. 1977, 87, 168342h
  • 4a Kleschick W, Her R, Gerwick B, Monte W, Pearson N, Costales M, and Meikle R. inventors; US Patent  4740233. 
  • 4b Selby T. Andrea T. Denes L. Finkelstein B. Fuesler T. Smith J. In Synthesis and Chemistry of Agrochemicals III   Baker D. Fenyes J. Steffens J. American Chemical Society; Washington DC: 1992.  p.91-102  
  • 5 Popova LM. Trishina AU. Vershilov SV. Ginak AL. Maksimov BN. J. Fluorine Chem  1999,  96:  51 
  • 6 Novinson T. Springer RH. O" Brien DE. Scholten MB. Miller JP. Robins RK. J. Med. Chem.  1982,  25:  420 ; and references therein
  • 7 Monte WT. Kleschick WA. Meikle RW. Snider SW. Bordner J. J. Heterocycl. Chem.  1989,  26:  1393 
  • 8a Allen CFH. Beilfuss HR. Burness DM. Reynolds GA. Tinker JF. Van Allan JA. J. Org. Chem.  1959,  24:  796 
  • 8b Bajwa JS. Sykes PJ. J. Chem. Soc., Perkin Trans. I  1979,  3085 
  • 9 Okabe T. Bhooshan B. Novinson T. Hillyard IW. Garner GE. Robins RK. J. Heterocycl. Chem.  1983,  20:  735 
  • 10 Chambers VC. J. Am. Chem. Soc.  1960,  82:  605 
  • 11 Hori M. Tanaka K. Kataoka T. Shimizu H. Imai E. Kimura K. Hashimoto Y. J. Chem. Soc., Perkin Trans. I  1985,  2333 
  • 12 Kleschick WA. Bordner J. J. Heterocycl. Chem.  1989,  26:  1489 
  • 13a Buelow C. Chem. Ber.  1909,  42:  4429 
  • 13b Bachkovskij IP. Chuiguk VA. Ykr. Khim. Z.  1987,  53:  319 
  • 13c Bajwa JS. Sykes PJ. J. Chem. Soc., Perkin Trans. I  1980,  1019 
  • 13d Russ T. Bats JW. Ried W. Synthesis  1990,  721 
  • 14a Mosby WL. In Heterocyclic Systems with Bridgehead Nitrogen Atoms   Wiley-Interscience; New York: 1961. 
  • 14b Wiessberger A. Taylor EC. In Special Topics in Heterocyclic Chemistry   Wiley-Interscience; New York: 1977. 
  • 15 Paudler W. Chao C. Helmick L. J. Heterocycl. Chem  1972,  1157 
  • 16 Petrich SA. Qian Z. Santiago LM. Gupton JT. Sikorski JA. Tetrahedron  1994,  50:  12113 
  • 17 Brown DJ. Nagamatsu T. Aust. J. Chem.  1977,  30:  2515 
  • 18 Krasovsky AL. Nenajdenko VG. Balenkova ES. Tetrahedron  2001,  1:  1349 
  • 19 Nenajdenko VG. Krasovsky AL. Lebedev ML. Balenkova ES. Synlett  1997,  1349 
  • 21 Krasovsky AL. Hartulyari A S. Nenajdenko VG. Balenkova ES. Syntheses  2002,  133 
  • 22 Krasovsky AL. Moiseev AM. Nenajdenko VG. Balenkova ES. Khim. Het. Soedin  2002,  253 
  • 24 Guerrel P. Jacquier R. Maury GJ. J. Heterocycl. Chem.  1971,  8:  643 
  • 25 Kawase M. Hirabayashi M. Saito S. Yamamoto K. Tetrahedron Lett.  1999,  40:  2541 
  • 26 Bouillon J.-P. Janousek Z. Viehe HG. Tinant B. Declercq J.-P. J. Chem. Soc., Perkin Trans. I  1995,  2907 
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Krasovsky, A. L.; Nenajdenko, V. G.; Balenkova, E. S. Synthesis 2002, in press.

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Krasovsky, A. L.; Moiseev A. M.; Nenajdenko, V. G.; Balenkova, E. S. Khim. Het. Soedin 2002, in press.