Synthesis of ethyl pyrimidine-4-carboxylates from unsymmetrical enamino diketones and their application in the first synthesis of pyrimido[4,5-d] pyridazin-8(7H)-ones

Synthesis

Volumn , Issue 22, 2008, Pages 3639-3648

  Rosa, Fernanda A ^a   Machado, Pablo ^a   Fiss, Gabriela F ^a   Vargas, Pamela S ^a   Fernandes, Tanize S ^a   Bonacorso, Helio G ^a   Zanatta, Nilo ^a   Martins, Marcos A P ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Cyclizations; Enones; Heterocycles; Pyrimidines; Regioselectivity; Ring closure

Indexed keywords

CARBOXYLATION; CYCLIZATION; REGIOSELECTIVITY; STEEL BEAMS AND GIRDERS;

CYCLIZATIONS; ENONES; HETEROCYCLES; PYRIMIDINES; RING CLOSURE;

KETONES;

2,5 DIPHENYLPYRIMIDO[4,5-D]PYRIDAZIN 8(7H)ONE; 5 (4 METHOXYPHENYL) 2 PHENYLPYRIMIDO[4,5-D]PYRIDAZIN 8(7H)ONE; ETHYL 2 (1H PYRAZOL 1 YL) 5 (2 THIENYLCARBONYL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 2 (2,4 DIPHENYLPYRIMIDIN 5 YL) 2 OXOACETATE; ETHYL 2 [2 (BENZOFURAN 2 YL) 2 PHENYLPYRIMIDIN 5 YL] 2 OXOACETATE; ETHYL 2 [2 PHENYL 4 (TRIFLUOROMETHYL)PYRIMIDIN 5 YL] 2 OXOACETATE; ETHYL 2 [4 (4 BROMOPHENYL) 2 PHENYLPYRIMIDIN 5 YL] 2 OXOACETATE; ETHYL 2 [4 (4 CHLOROPHENYL) 2 PHENYLPYRIMIDIN 5 YL] 2 OXOACETATE; ETHYL 2 [4 (4 NITROPHENYL) 2 PHENYLPYRIMIDIN 5 YL] 2 OXOACETATE; ETHYL 2 PHENYL 5 (2 THIENYLCARBONYL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 BROMOBENZOYL 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 BROMOBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 CHLOROBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 CHLOROBENZOYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 FLUOROBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 FLUOROBENZOYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 METHOXYBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 METHOXYBENZOYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 METHYLBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 METHYLBENZOYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 NITROBENZOYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (4 NITROBENZOYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (BENZOFURAN 2 CARBONYL) 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; ETHYL 5 (BENZOFURAN 2 YL CARBONYL) 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 BENZOYL 2 (1H PYRAZOL 1 YL)PYRIMIDINE 4 CARBOXYLATE; ETHYL 5 BENZOYL 2 PHENYLPYRIMIDINE 4 CARBOXYLATE; KETONE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRIMIDO[4,5-D]PYRIDAZIN 8(7H)ONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS;

EID: 58849148545     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083202     Document Type: Article

References (27)

1. (a) Nargund, L. V. G.; Badiger, V. V.; Yarnal, S. U. Eur. J. Med. Chem. 1994, 29, 245.
2. (b) Ouf, N. H.; Amr A. El-G, E.; Fayed, A. A. Monatsh. Chem. 2008, 139, 281.
3. (c) Tafi, A.; Bemardine, C; Botta, M; Corelli, F.; Andreini, ML; Martineli, A.; Ortore, G.; Baraldi, P. G.; Fruttarolo, F.; Borea, P. A.; Tuccinardi, T. J. Med Chem. 2006, 49, 4085.
4. (d) Orjales, A.; Mosquera, R.; López, B.; Olivera, R.; Labeaga, L.; Núñez, M. T. Bioorg. Med. Chem. 2008, 16, 2183.
5. (e) Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med Chem. 1998, 41, 191; and references therein.
6. (a) Brown, D. J. In Comprehensive Heterocyclic Chemistry, Vol. 3; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984.
7. (b) Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II, Vol. 6; Katritzky, A. R.; Rees, C. W.; Scriven," E. F., Eds.; Pergamon: Oxford, 1996.
8. (c) Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G. Chem. Rev. 2008, 108, 2015.
9. (d) 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.
10. (a) Jones, R. G.; Whitehead, C. W. J. Org. Chem. 1955, 20, 1342.
11. (b) Krapcho, A. P.; Maresch, M. J.; Helgason, A. L.; Rosner, K. E.; Hacker, M. P. J. Heterocycl. Chem. 1993, 30, 1597.
12. Bradshaw, J. S.; Huszthy, P.; Izatt, R. M. J. Heterocycl Chem. 1994, 31, 1047.
13. Riley, T. A.; Hennen, W. J.; Dalley, N. K.; Wilson, B. E.; Robins, R. K.; Larson, S. B. J. Heterocycl. Chem. 1987, 24, 955.
14. Jones, R. G. J. Am. Chem. Soc. 1956, 78, 159.
15. (a) Kuderna, J. G.; Skiles, R. D.; Pilgram, K. J. Org. Chem. 1971, 36, 3506.
16. (b) Matyus, P.; Szilagyi, G.; Kasztreiner, E.; Rabloczky, G. J. Heterocycl. Chem. 1988, 25, 1535.
17. Treu, M.; Jordis, U.; Lee, V. J. Molecules 2001, 6, 959.
18. Rosa, F. A.; Machado, P.; Rossatto, M.; Vargas, P. S.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Synlett 2007, 3165.
19. Rosa, F. A.; Machado, P.; Vargas, P. S.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Synlett 2008, 1673.
20. Crystallographic data for compounds 4a, 6h, and 7a reported in this paper, have been deposited with the Cambridge Crystallographic Data Centre(CCDC Number 686848, 686847, and 687296, respectively). Copies of the data can be obtained, free of charge, on application to CCDC 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
21. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
22. Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
23. HYPERCHEM™ Professional 7.52(2002), Hypercube, Inc.: 1115 NW 4th Street, Gainesville, FL 32601, USA.
24. Echevarria, A.; Elguero, J.; Llamas-Saiz, A. L.; Foces-Foces, C.; Schultz, G.; Hargittai. I. Struct. Chem. 1994, 5. 255.
25. Perrin, D. D.; Armarego, W. L. F. In Purification of Laboratory Chemicals; Pergamon: Oxford, 1998.
26. SHELXTL 6.14, Bruker AXS Inc.: Madison WI, 2003.
27. Farrugia. L. J. J. Appl. Crystallogr. 1999, 32, 837.