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Synthesis 2009(19): 3233-3242
DOI: 10.1055/s-0029-1216957
DOI: 10.1055/s-0029-1216957
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
3-(Polyfluoroacyl)chromones and Their Hetero Analogues as Valuable Substrates for Syntheses of 4-(Polyfluoroalkyl)pyrimidines
Further Information
Received
23 February 2009
Publication Date:
21 August 2009 (online)
Publication History
Publication Date:
21 August 2009 (online)
Abstract
Reactions of 3-(polyfluoroacyl)chromones and their hetero analogues with a number of 1,3-NCN-dinucleophiles, such as amidines or guanidines, were studied in detail, and preparative access to a set of diverse 5-salicyloyl-4-(polyfluoroalkyl)pyrimidines was elaborated. These compounds appear to be a suitable starting substrates for the synthesis of 4-(polyfluoroalkyl)pyrimidine-5-carboxylic acids or pyrimidines containing a benzofuran-3-yl substituent in the 5-position.
Key words
chromones - thiochromones - fluorine - pyrimidine core annulation - regioselectivity - heterocycles
-
1a
Ghosh CK. J. Heterocycl. Chem. 1983, 20: 1437 -
1b
Sabitha G. Aldrichimica Acta 1996, 29: 15 -
1c
Sosnovskikh VYa.Moshkin VS.Kodess MI. Tetrahedron Lett. 2008, 49: 6856 -
2a
Petersen U.Heitzer H. Justus Liebigs Ann. Chem. 1976, 1663 -
2b
Löwe W. Synthesis 1976, 274 -
2c
Löwe W. Arch. Pharm. (Weinheim, Ger.) 1977, 310: 559 -
2d
Löwe W. Justus Liebigs Ann. Chem. 1977, 1050 -
2e
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Pipko SE.Tolmachev AA. Heterocycles 2008, 75: 583 -
2f
Randhavane PV.Kale SB.Jagdhani SG.Karale BK. Indian J. Heterocycl. Chem. 2007, 17: 153 -
2g
Sonawane SA.Karale BK.Shingare MS. Indian J. Heterocycl. Chem. 2004, 14: 155 -
3a
Orjales A.Mosquera R.López B.Olivera R.Labeaga L.Núñez MT. Bioorg. Med. Chem. 2008, 16: 2183 -
3b
Prevost G,Liberatore AM,Bigg D, andPons D. inventors; FR 2915747. ; Chem. Abstr. 2008, 149, 534244 - 4
Giblin GMP.O’Shaughnessy CT.Naylor A.Mitchell WL.Eatherton AJ.Slingsby BP.Rawlings DA.Goldsmith P.Brown AJ.Haslam CP.Clayton NM.Wilson AW.Chessell IP.Wittington AR.Green R. J. Med. Chem. 2007, 50: 2597 -
5a
Funabiki K.Nakamura H.Matsui M.Shibata K. Synlett 1999, 756 -
5b
Sevenard DV.Khomutov OG.Koryakova OV.Sattarova VV.Kodess MI.Stelten J.Loop I.Lork E.Pashkevich KI.Röschenthaler G.-V. Synthesis 2000, 1738 -
5c
Zanatta N.Cortelini M. de FM.Carpes MJS.Bonacorso HG.Martins MAP. J. Heterocycl. Chem. 1997, 34: 509 -
5d
Soufyane M.van den Broek S.Khamliche L.Mirand C. Heterocycles 1999, 51: 2445 -
5e
Yu H.-B.Huang W.-Y. J. Fluorine Chem. 1997, 84: 65 -
5f
Soufyane M.Mirand C.Lévy J. Tetrahedron Lett. 1993, 34: 7737 -
5g
Sosnovskikh VYa.Usachev BI.Röschenthaler G.-V. Tetrahedron 2002, 58: 1375 -
5h
Sosnovskikh VYa.Usachev BI.Sizov AYu.Barabanov MA. Synthesis 2004, 942 - 6
Schlosser M.Lefebvre O.Ondi L. Eur. J. Org. Chem. 2006, 1593 - 7
Uneyama K. Organofluorine Chemistry Blackwell; Oxford: 2006. -
8a
Iaroshenko VO.Volochnyuk DM.Wang Y.Vovk MV.Boiko VJ.Rusanov EB.Groth UM.Tolmachev AO. Synthesis 2007, 3309 -
8b
Iaroshenko VO.Sevenard DV.Kotljarov AV.Volochnyuk DM.Tolmachev AO.Sosnovskikh VYa. Synthesis 2009, 731 -
8c
Dang Q.Liu Y.Sun Z. Tetrahedron Lett. 2001, 42: 8419 - 9
Yokoe I.Maruyama K.Sugita Y.Harashida T.Shirataki Y. Chem. Pharm. Bull. 1994, 42: 1697 -
10a
Sosnovskikh VYa.Irgashev RA. Synlett 2005, 1164 -
10b
Sosnovskikh VYa.Irgashev RA.Barabanov MA. Synthesis 2006, 2707 -
10c
Sosnovskikh VYa.Irgashev RA. Heteroat. Chem. 2006, 17: 99 - 11
Hiyama T. Organofluorine Compounds: Chemistry and Application Springer-Verlag; Berlin: 2000. - 12
Löwe W.Jeske P. Liebigs Ann. Chem. 1986, 1124 - 13
Sevenard DV.Vorobyev M.Sosnovskikh V. Ya.Wessel H.Kazakova O.Vogel V.Shevchenko N. E.Nanajdenko V. G.Lork E.Röschenthaler G.-V. Tetrahedron 2009, 65: 7538 - 14
Sosnovskikh VYa.Barabanov MA. J. Fluorine Chem. 2003, 120: 25 - 15
Yamada K,Matsuki K,Omori K, andKikkawa K. inventors; US 2004142930. ; Chem. Abstr. 2004, 141, 140463 - 16
Puccetti L.Fasolis G.Vullo D.Chohan ZH.Scozzafava A.Supuran CT. Bioorg. Med. Chem. Lett. 2005, 15: 3096 -
17a
Tseng PW.Yeh SW.Chou CH. J. Org. Chem. 2008, 73: 3481 -
17b
Kobayashi K.Nakamura D.Fukamachi S.Konishi H. Heterocycles 2008, 75: 919 -
18a
Dorigo P.Fraccarollo D.Santostasi G.Maragno IM.Floreani M.Borea PA.Mosti L.Sansebastiano L.Fossa P.Orsini F.Benetollo F.Bombieri G. J. Med. Chem. 1996, 39: 3671 -
18b
Sansebastiano L.Mosti L.Menozzi G.Schenone P.Muratore O.Petta A.Debbia E.Schito AP.Schito GC. Farmaco 1993, 48: 335 -
18c
Lahm GP.Selby TP.Freudenberger JH.Stevenson TM.Myers BJ.Seburyamo G.Smith BK.Flexner L.Clark CE.Cordova D. Bioorg. Med. Chem. Lett. 2005, 15: 4898 -
18d
Palanki MSS.Erdman PE.Gayo-Fung LM.Shevlin GI.Sullivan RW.Goldman ME.Ransone LJ.Bennett BL.Manning AM.Suto MJ. J. Med. Chem. 2000, 43: 3995 -
18e
Palanki MSS.Gayo-Fung LM.Shevlin GI.Erdman P.Sato M.Goldman M.Ransone LJ.Spooner C. Bioorg. Med. Chem. Lett. 2002, 12: 2573 - 19
Bodwell GJ.Hawco KM.Satou T. Synlett 2003, 879