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Synthesis 2002(7): 0901-0905
DOI: 10.1055/s-2002-28512
DOI: 10.1055/s-2002-28512
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of New Fluorine Containing Triazolo- and Tetrazolopyrimidines
Weitere Informationen
Received
5 February 2002
Publikationsdatum:
14. Mai 2002 (online)
Publikationsverlauf
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.
Key words
cycloaddition - heterocycles - triazolopyrimidine - tetrazolopyrimidine - sulfones
-
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, andDuerr D. inventors; EP 337944. ; Chem. Abstr. 1990, 112, 139043r -
2b
Rempfler H,Duerr D, andThummel 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, andSidorov B. inventors; US Patent 4039546. ; Chem. Abstr. 1977, 87, 168342h -
4a
Kleschick W,Her R,Gerwick B,Monte W,Pearson N,Costales M, andMeikle R. inventors; US Patent 4740233. -
4b
Selby T.Andrea T.Denes L.Finkelstein B.Fuesler T.Smith J. In Synthesis and Chemistry of Agrochemicals IIIBaker 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
References
Krasovsky, A. L.; Nenajdenko, V. G.; Balenkova, E. S. Synthesis 2002, in press.
23Krasovsky, A. L.; Moiseev A. M.; Nenajdenko, V. G.; Balenkova, E. S. Khim. Het. Soedin 2002, in press.