Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(14): 2349-2356
DOI: 10.1055/s-2006-942431
DOI: 10.1055/s-2006-942431
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of New 2-(5-Aryl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines
Further Information
Received
14 October 2005
Publication Date:
26 June 2006 (online)
Publication History
Publication Date:
26 June 2006 (online)
Abstract
A series of 2-(5-aryl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines was synthesized by the cyclocondensation of 5-aryl-1-carboxamidino-3-styryl-4,5-dihydro-1H-pyrazoles with 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones. Efficient cyclizations catalyzed by Ti(Oi-Pr)4 or BF3·OEt2 gave the desired pyrimidines in good yields. The crystal structure of ethyl 3-[2-(5-phenyl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidin-6-yl]propanoate was determined.
Key words
1H-pyrazoles - pyrimidines - homogeneous catalysis
- 1
Chimenti F.Bolasco A.Manna F.Secci D.Chimenti P.Befani O.Turini P.Giovannini V.Mondovi B.Cirilli R.La Torre F. J. Med. Chem. 2004, 47: 2071 - 2
Meier H.Hormaza A. Eur. J. Org. Chem. 2003, 3372 - 3
Lévai A. J. Heterocycl. Chem. 2002, 39: 1 - 4
Palaska E.Aytemir M.Uzbay IT.Erol D. Eur. J. Med. Chem. 2001, 36: 539 - 5
Zanatta N.Flores DC.Madruga CC.Faoro D.Flores AFC.Bonacorso HG.Martins MAP. Synthesis 2003, 894 -
6a
Bonacorso HG.Wentz AP.Zanatta N.Martins MAP. Synthesis 2001, 1505 -
6b
Bonacorso HG.Martins DB.Martins MAP.Zanatta N.Flores AFC. Synthesis 2005, 809 - 7
Huang YR.Katzenellenbogen JA. Org. Lett. 2000, 2: 2833 - 8
Fu H.Xiao D.Xie R.Ji X.Yao J.-N. Can. J. Chem. 2003, 81: 7 - 9
Fahrni CJ.Yang L.VanDerveer DG. J. Am. Chem. Soc. 2003, 125: 3799 - 10
Xiao D.Xi L.Yang W.Fu H.Shuai Z.Fang Y.Yao J. J. Am. Chem. Soc. 2003, 125: 6740 - 11
Wha OhS.Ri Zhang D.Soo Kang Y. Mater. Sci. Eng., C 2004, 24: 131 - 12
Zhang XH.Lai WY.Gao ZQ.Wong TC.Lee CS.Kwong HL.Lee ST.Wu SK. Chem. Phys. Lett. 2000, 320: 77 - 13
Lévai A.Patonay T.Silva AMS.Pinto DCGA.Cavaleiro JAS. J. Heterocycl. Chem. 2002, 39: 751 -
14a
Azarifar D.Shaebanzadeh M. Molecules 2002, 7: 885 -
14b
Vijayabaskar V.Perumal S.Selvaraj S.Lycka A.Murugan R.Balasubramanian M. Magn. Reson. Chem. 1999, 37: 133 - 15
Nauduri D.Reddy GBS. Chem. Pharm. Bull. 1998, 46: 1254 - 16
Dove MFA.Sanders JCP.Appelman EH. Magn. Reson. Chem. 1995, 33: 44 - 17
Sevenard DV.Khomutov OG.Koryakova OV.Sattarova VV.Kodess MI.Stelten J.Loop I.Lork E.Pashkevich KI.Röschenthaler G.-V. Synthesis 2000, 1738 - 18
Berger S.Braun S.Kalinowski H.-O. NMR Spectroscopy of the Non-metallic Elements Wiley; Chichester: 1997. p.398-400 - 19 SHELXTL 6.14 Bruker AXS Inc.; Madison WI: 2003.
- 20
Farrugia LJ. J. Appl. Crystallogr. 1999, 32: 837