Synthesis of New 2-(5-Aryl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines

Darlene C. Flores; Gabriela F. Fiss; Letícia S. Wbatuba; Marcos A. P. Martins; Robert A. Burrow; Alex F. C. Flores

doi:10.1055/s-2006-942431

PAPER

Synthesis of New 2-(5-Aryl-3-styryl-4,5-dihydro-1H-pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines

Darlene C. Flores^a, Gabriela F. Fiss^a, Letícia S. Wbatuba^b, Marcos A. P. Martins^a, Robert A. Burrow^a, Alex F. C. Flores*^a
^a NUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, 97105 900 Santa Maria, RS, Brazil
^b Departamento de Farmácia, Centro Universitário Franciscano, Andradas 1614, 97010 032 Santa Maria, RS, Brazil
Fax: +55(55)32208031; e-Mail: alexflores@smail.ufsm.br;

Abstract

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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

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Referenzen

References

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