A convenient synthesis of 5- and 6-substituted 2-phenyl-3H-pyrimidin-4-ones

Synthesis

Volumn , Issue 3, 2008, Pages 0358-0362

  Zanatta, Nilo ^a   Fantinel, Leonardo ^a   Lourega, Rogério V ^a   Bonacorso, Helio G ^a   Martins, Marcos A P ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

2 phenylpyrimidin 4 ones; Benzamidine hydrochloride; Pyrimidines; Sildenafil; Trichloromethylated enones

Indexed keywords

2-PHENYLPYRIMIDIN-4-ONES; BENZAMIDINE HYDROCHLORIDE; TRICHLOROMETHYLATED ENONES;

CONDENSATION; SYNTHESIS (CHEMICAL);

KETONES;

2 PHENYL 4 (4 TOLYL) 6 (TRICHLOROMETHYL)PYRIMIDINE; 2 PHENYL 4A,5,6,7 TETRAHYDRO 3H PYRANO[2,3 D]PYRIMIDIN 4(8AH) ONE; 2 PHENYL 6 (4 TOLYL)PYRIMIDIN 4(3H) ONE; 2 PHENYL 6 PROPYLPYRIMIDIN 4(3H) ONE; 2 PHENYLPYRIMIDIN 4(3H) ONE; 2,6 DIPHENYLPYRIMIDIN 4(3H) ONE; 3 PHENYL 5,6 DIHYDROFURO[2,3 D]PYRIMIDIN 4(3H,4AH,7AH) ONE; 4 (4 BROMOPHENYL) 2 PHENYL 6 (TRICHLOROMETHYL)PYRIMIDINE; 4 (4 CHLOROPHENYL) 2 PHENYL 6 (TRICHLOROMETHYL)PYRIMIDINE; 4 (4 METHOXYPHENYL) 2 PHENYL 6 (TRICHLOROMETHYL)PYRIMIDINE; 6 (4 BROMOPHENYL) 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 (4 CHLOROPHENYL) 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 (4 METHOXYPHENYL) 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 (BROMOMETHYL) 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 BUTYL 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 ETHOXY 5 METHYL 2 PHENYL 5,6 DEHYDROPYRIMIDIN 4(3H) ONE; 6 ETHYL 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 ISOBUTYL 2 PHENYLPYRIMIDIN 4(3H) ONE; 6 METHYL 2 PHENYLPYRIMIDIN 4(3H) ONE; BENZAMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; POLYMERIZATION;

EID: 39349116785     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032032     Document Type: Article

References (29)

1. Murphy, R.; Kung, H. F.; Kung, M.; Billings, J. J. Med. Chem. 1990, 33, 171.
2. (a) Langtry, H. D.; Markham, A. Drugs 1999, 57, 967.
3. (b) Moreland, R. B.; Goldstein, I.; Kim, N. N.; Traish, A. Trends Endocrinol. Metab. 1999, 44, 153.
4. Akazome, M.; Kondo, T.; Watanabe, Y. J. Mol. Catal. 1993, 80, 383.
5. Burdeska, K.; Fuhrer, H.; Kabas, G.; Siergrist, A. E. Helv. Chim. Acta 1981, 64, 113.
6. (a) Katritzky, A. R.; Yousaf, T. I. Can. J. Chem. 1986, 64, 2087.
7. (b) Hamper, B. C.; Gan, K. Z.; Owen, T. J. Tetrahedron Lett. 1999, 40, 4973.
8. Marsura, A.; Luu Duc, C. Synthesis 1982, 595.
9. Kato, T.; Chiba, T.; Sasaki, M. Heterocycles 1981, 16, 577.
10. Gallemaers, J.-P.; Christophe, D.; Promel, R. Tetrahedron Lett. 1976, 693.
11. Yamamoto, Y.; Ohnishi, S.; Azuma, Y. Chem. Pharm. Bull. 1983, 31, 1929.
12. Hirai, Y.; Egawa, H.; Shoko, Y.; Yamazaki, T. Heterocycles 1983, 20, 1243.
13. (a) Tice, C. M.; Bryman, L. M. Tetrahedron 2001, 57, 2689.
14. (b) Chang, L. C. W.; Spangersberg, R. F.; von Frijtag Drabbe Künzel, J. K.; Mulder-Krieger, T.; van den Hout, G.; Beukers, M. W.; Brussee, J.; Ijzerman, A. P. J. Med. Chem. 2004, 47, 6529.
15. Hamper, B. C.; Gan, K. Z.; Owen, T. J. Tetrahedron Lett. 1999, 40, 4973.
16. Colla, A.; Martins, M. A. P.; Clar, G.; Krimmer, S.; Fisher, P. Synthesis 1991, 483.
17. (a) Martins, M. A. P.; Siqueira, G. M.; Flores, A. F. C.; Clar, G.; Zanatta, N. Quím. Nova 1994, 17, 24.
18. (b) Martins, M. A. P.; Bastos, G. P.; Bonacorso, H. G.; Zanatta, N.; Flores, A. F. C.; Siqueira, G. M. Tetrahedron Lett. 1999, 40, 4309.
19. Zanatta, N.; Barichello, R.; Pauletto, M.; Bonacorso, H. G.; Martins, M. A. P. Tetrahedron Lett. 2003, 44, 961.
20. Martins, M. A. P.; Pereira, C. M. P.; Beck, P.; Machado, P.; Moura, S.; Teixeira, M. V. M.; Bonacorso, H. G.; Zanatta, N. Tetrahedron Lett. 2003, 44, 6669.
21. Zanatta, N.; Faoro, D.; Silva, S. C.; Bonacorso, H. G.; Martins, M. A. P. Tetrahedron Lett. 2004, 45, 5689.
22. Martins, M. A. P.; Emmerich, D.; Beck, P.; Cunico, W.; Pereira, C. M. P.; Sinhorin, A. P.; Brondani, S.; Peres, R. L.; Teixeira, M. V. M.; Bonacorso, H. G.; Zanatta, N. Synth. Commun. 2004, 34, 1915.
23. Zanatta, N.; Flores, D. C.; Amaral, S. S.; Bonacorso, H. G.; Martins, M. A. P.; Flores, A. F. C. Synlett 2005, 3079.
24. Zanatta, N.; Flores, D. C.; Madruga, C. C.; Flores, A. F. C.; Bonacorso, H. G.; Martins, M. A. P. Tetrahedron Lett. 2006, 47, 573.
25. Martins, M. A. P.; Cunico, W.; Pereira, C. M. P.; Sinhorin, A. P.; Flores, A. F. C.; Bonacorso, H. G.; Zanatta, N. Curr. Org. Synth. 2004, 1, 391.
26. Zanatta, N.; Cortelini, M. F. M.; Carpes, M. J. S.; Bonacorso, H. G.; Martins, M. A. P. J. Heterocycl. Chem. 1997, 34, 509.
27. Zanatta, N.; Flores, D. C.; Madruga, C. C.; Flores, A. F. C.; Bonacorso, H. G.; Martins, M. A. P. Tetrahedron Lett. 2006, 47, 573.
28. Zanatta, N.; Fagundes, M. B.; Ellensohn, R.; Marques, M.; Bonacorso, H. G.; Martins, M. A. P. J. Heterocycl. Chem. 1998, 35, 451.
29. Zanatta, N.; Faoro, D.; Silva, S. C.; Bonacorso, H. G.; Martins, M. A. P. Tetrahedron Lett. 2004, 45, 5689.