A convenient synthesis of 4-trifluoromethyl-(2H)-pyridazin-3-ones from methyl 3,3,3-trifluoropyruvate

Synlett

Volumn , Issue 12, 2005, Pages 1907-1911

  Sibgatulin, Dmitriy A ^a   Volochnyuk, Dmitriy M ^a   Kostyuk, Alexandr N ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Aldol condensation; Cyclocondensation; Methyl 3,3,3 trifluoropyruvate; Pyridazinones; Trifluoromethyl

Indexed keywords

4 TRIFLUOROMETHYL (2H) PYRIDAZIN 3 ONE; METHYL 3,3,3 TRIFLUOROPYRUVATE; PYRIDAZINE DERIVATIVE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MELTING POINT; REACTION TIME; SYNTHESIS;

EID: 23644443196     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871926     Document Type: Article

References (28)

1. Conteras, J.-M.; Rival, Y. M.; Chayer, S.; Bourguignon, J.-J.; Wermuth, C. G. J. Med. Chem. 1999, 42, 730.
2. (a) Yoshinori, K.; Tomoyuki, K.; Hiromichi, S.; Hideo, Y.; Takahiro, K.; Shunji, T.; Kyoko, Y.; Junko, T.; Seiichi, S. U.S. Pat. Appl. Publ. US 2004002497, 2004; Chem. Abstr. 2004, 140, 77155.
3. (b) Matyus, P.; Maes, B. U. W.; Riedl, Z.; Hajos, G.; Lemiere, G. L. F.; Tapolcsanyi, P.; Monsieurs, K.; Elias, O.; Dommisse, R. A.; Krajsovszky, G. Synlett 2004, 1123; and references therein.
4. (a) Brule, C.; Bouillon, J.-P.; Nicolai, E.; Portella, C. Synthesis 2003, 436.
5. (b) Kamitori, Y.; Sekiyama, T. Heterocycles 2004, 63, 707.
6. (a) Fluorine in Bioorganic Chemistry; Filler, R.; Kobayasi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993.
7. (b) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: Chichester, 1992.
8. (c) Kukhar, V. P.; Soloshonok, V. A. Fluorine-Containing Amino Acids, Synthesis and Properties; Wiley: New York, 1995.
9. (a) Wermuth, C. G.; Schlewer, G.; Bourguignon, J.-J.; Maghioros, G.; Bouchet, M.-J.; Moire, C.; Kan, J.-P.; Worms, P.; Biziere, K. J. Med. Chem. 1989, 32, 528.
10. (b) Coates, W. J.; McKillop, A. Synthesis 1992, 334.
11. (c) Baraldi, P. G.; Bigoni, A.; Cacciari, B.; Caldari, C.; Manfredini, S.; Spalluto, G. Synthesis 1994, 1158.
12. (d) Yoshida, N.; Awano, K.; Kobayashi, T.; Fujimori, K. Synthesis 2004, 1554.
13. (a) Golubiev, A. S.; Galakhov, M. V.; Kolomiets, A. F.; Fokin, A. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 9, 2127.
14. (b) Palecec, J.; Paleta, O. Synthesis 2004, 521.
15. Volochnyuk, D. M.; Kostyuk, A. N.; Sibgatulin, D. A.; Petrenko, A. E. Synthesis 2004, 2545.
16. Paleta, O.; Palesek, J.; Dolensky, B. J. Fluorine Chem. 2001, 111, 175.
17. Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2001, 66, 1009.
18. 19F NMR). After cooling the tube was opened (Caution! Excessive pressure inside!) and the residue was triturated with n-hexane yielding targeted compound 7.
19. HH = 4.8 Hz, CH).
20. CF = 285.3 Hz), 128.4, 133.1, 135.1, 142.7, 169.2, 187.4.
21. +], 39 (16).
22. 2O affording 8.
23. 6): δ = 7.18 (1 H, s, CH), 7.69 (1 H, s, CH), 7.91 (1 H, s, CH), 8.47 (1 H, s, CH), 13.73 (1 H, s, NH).
24. CF = 4.9 Hz), 138.3, 140.3, 156.0.
25. +], 189(54).
26. +], 148 (15), 120 (39), 106 (14), 75 (19).
27. + - MeTFP].
28. +-MeTFP].