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Synthesis 2004(6): 942-948
DOI: 10.1055/s-2004-822321
DOI: 10.1055/s-2004-822321
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Simple One-Pot Synthesis of 2,6-Disubstituted 4-(Polyfluoroalkyl)pyridines and -pyrimidines by Reaction of 2-Polyfluoroalkylchromones with Aromatic Methyl Ketimines and Amidines
Further Information
Received
4 February 2004
Publication Date:
25 March 2004 (online)
Publication History
Publication Date:
25 March 2004 (online)
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Abstract
The reaction of 2-polyfluoroalkylchromones with ketimines, derived from aromatic methyl ketones and isopropylamine, gives 2,6-diaryl-4-polyfluoroalkylpyridines in moderate to low yields. Benzamidine and guanidine also react with 2-polyfluoroalkylchromones to afford the corresponding 2,6-disubstituted 4-polyfluoroalkylpyrimidines.
Key words
2-polyfluoroalkylchromones - ketimines - amidines - 4-polyfluoroalkylpyridines and -pyrimidines
-
1a
Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
Filler R.Kobayashi Y.Yagupolskii LM. Elsevier; Amsterdam: 1993. -
1b
Welch JT.Eswarakrishnan S. Fluorine in Bioorganic Chemistry Wiley; New York: 1991. -
1c
Hiyama T. Organofluorine Compounds. Chemistry and Application Springer-Verlag; Berlin: 2000. -
2a
McClinton MA.McClinton DA. Tetrahedron 1992, 48: 6555 -
2b
Lin P.Jiang J. Tetrahedron 2000, 56: 3635 -
2c
Nenaidenko VG.Sanin AV.Balenkova ES. Russ. Chem. Rev. 1999, 68: 437 -
2d
Sosnovskikh VYa. Russ. Chem. Rev. 2003, 72: 489 -
3a
Funabiki K.Isomura A.Yamaguchi Y.Hashimoto W.Matsunaga K.Shibata K.Matsui M. J. Chem. Soc., Perkin Trans. 1 2001, 2578 -
3b
Katsuyama I.Ogawa S.Yamaguchi Y.Funabiki K.Matsui M.Muramatsu H.Shibata K. Synthesis 1997, 1321 -
3c
Katsuyama I.Funabiki K.Matsui M.Muramatsu H.Shibata K. Synlett 1997, 591 -
3d
Konakahara T.Hojahmat M.Tamura S. J. Chem. Soc., Perkin Trans. 1 1999, 2803 -
3e
Lee LF.Stikes GL.Molyneaux JM.Sing YL.Chupp JP.Woodard SS. J. Org. Chem. 1990, 55: 2872 -
3f
Lee LF. inventors; Eur. Pat. Appl. EP 0133612, 1985; Chem. Abstr. 1986, 104. -
3g
Xiong W.-N.Yang C.-G.Jiang B. Bioorg. Med. Chem. 2001, 9: 1773 -
4a
Guan H.-P.Hu Q.-S.Hu C.-M. Synthesis 1996, 997 -
4b
Funabiki K.Nakamura H.Matsui M.Shibata K. Synlett 1999, 756 -
4c
Sevenard DV.Khomutov OG.Koryakova OV.Sattarova VV.Kodess MI.Stelten J.Loop I.Lork E.Pashkevich KI.Röschenthaler G.-V. Synthesis 2000, 1738 -
4d
Zanatta N.Cortelini M.Carpes MJS.Bonacorso HG.Martins MAP. J. Heterocycl. Chem. 1997, 34: 509 -
4e
Madruga C.Clerici E.Martins MAP.Zanatta N. J. Heterocycl. Chem. 1995, 32: 735 -
4f
Zanatta N.Fagundes MB.Ellensohn R.Marques M.Bonacorso HG.Martins MAP. J. Heterocycl. Chem. 1998, 35: 451 -
4g
Soufyane M.van den Broek S.Khamliche L.Mirand C. Heterocycles 1999, 51: 2445 -
4h
Yu H.-B.Huang W.-Y. J. Fluorine Chem. 1997, 84: 65 -
4i
Yu H.-B.Huang W.-Y. J. Fluorine Chem. 1998, 87: 69 -
4j
Guan H.-P.Tang X.-Q.Luo B.-H.Hu C.-M. Synthesis 1997, 1489 -
4k
Frasinyuk MS.Khilya VP. Chem. Heterocycl. Compd. 1999, 35: 3 -
4l
Luo B.-H.Guang H.-P.Hu C.-M. Synlett 1997, 1261 -
4m
Sosnovskikh VYa.Usachev BI.Röschenthaler G.-V. Tetrahedron 2002, 58: 1375 -
4n
Burger K.Hein F.Wassmuth U.Krist H. Synthesis 1981, 904 - 5
Sosnovskikh VYa.Usachev BI.Sizov AYu.Vorontsov II.Shklyaev VYu. Org. Lett. 2003, 5: 3123 -
6a
Sosnovskikh VYa.Usachev BI. Russ. Chem. Bull. 2001, 50: 453 -
6b
Sosnovskikh VYa.Vorontsov II.Kutsenko VA. Russ. Chem. Bull. 2001, 50: 1430 -
6c
Sosnovskikh VYa.Usachev BI.Sevenard DV.Röschenthaler G.-V. Tetrahedron 2003, 59: 2625 -
6d
Sosnovskikh VYa.Usachev BI.Vorontsov II. Tetrahedron 2003, 59: 2549 -
6e
Sosnovskikh VYa.Sevenard DV.Usachev BI.Röschenthaler G.-V. Tetrahedron Lett. 2003, 44: 2097 -
6f
Sosnovskikh VYa.Usachev BI.Sevenard DV.Röschenthaler G.-V. J. Org. Chem. 2003, 68: 7747 -
7a
Sosnovskikh VYa.Kutsenko VA. Mendeleev Commun. 2000, 238 -
7b
Whalley WB. J. Chem. Soc. 1951, 3235 -
8a
Tong H.Zhou G.Wang L.Jing X.Wang F.Zhang J. Tetrahedron Lett. 2003, 44: 131 -
8b
Li Y.Liu Y.Bu W.Guo J.Wang Y. Chem. Commun. 2000, 1551 -
8c
Wang Y,Wu Y,Li Y,Liu Y,Lu D, andShen J. inventors; Canadian Patent CN 1245822. ; Chem. Abstr. 2000, 133, 315395 -
8d
Ueno K,Suzuki K,Senoo A,Tanabe H, andYogi S. inventors; Eur. Pat. Appl. EP 1138683. ; Chem. Abstr. 2001, 135, 257340 - 9
Sosnovskikh VYa.Barabanov MA. J. Fluorine Chem. 2003, 120: 25 -
10a
Weingarten H.Chupp JP.White WA. J. Org. Chem. 1967, 32: 3246 -
10b
Snyder HR.Matteson DS. J. Am. Chem. Soc. 1957, 79: 2217 - 11
Pickard PL.Vaughan DJ. J. Am. Chem. Soc. 1950, 72: 876