Synthesis of new polyfluoroalkyl-containing pyrones, pyridones and pyrido[1,2-a]benzazoles from fluorinated β-alkoxyenones

Synthesis

Volumn , Issue 24, 2007, Pages 3797-3806

  Tolmachova, Nataliya A ^a   Gerus, Igor I ^a   Vdovenko, Sergey I ^a   Haufe, Günter ^b   Kirzhner, Yuriy A ^c  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c ENAMINE LTD   (Ukraine)

Author keywords

2H pyran 2 ones; Enones; Heterocycles; Polyfluoroalkyl group; Pyridine

Indexed keywords

ENONES; HETEROCYCLES; NUCLEOPHILIC ATTACK; POLYFLUOROALKYL GROUP; THIAZOLES;

ESTERS; FUNCTIONAL GROUPS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

KETONES;

1 HYDROXY 5 METHYL 2 (TRIFLUOROACETYL) 1 (TRIFLUOROMETHYL) 1,5 DIHYDROPYRIDO[1,2 A]BENZIMIDAZOLE 4 CARBONITRILE; 3 METHYL 5 (TRIFLUOROMETHYL)IMIDAZO[1,2 A]PYRIDINE 8 CARBONITRILE; 4 (PHENYLSULFONYL) 1 (TRIFLUOROMETHYL)PYRIDO[1,2 A]BENZIMIDAZOLE; 6,6,6 TRIFLUORO 2 (1 METHYL 1,3 DIHYDRO 2H BENZIMIDAZOL 2 YLIDENE) 5 OXO 4 (TRIFLUOROACETYL)HEX 3 ENENITRILE; 6,6,6 TRIFLUORO 2 (4 METHYL 1,3 DIHYDRO 2H IMIDAZOL 2 YLIDENE) 5 OXOHEX 3 ENENITRILE; BETA ALKOXYENONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; FLUORINE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; METHYL 1 HYDROXY 2 (TRIFLUOROACETYL) 1 (TRIFLUOROMETHYL) 1,5 DIHYDROPYRIDO[1,2 ALPHA]BENZIMIDAZOLE 4 CARBOXYLATE; PYRIDO[1,2 A]BENZAZOLE DERIVATIVE; PYRIDONE DERIVATIVE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION;

EID: 37549046363     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990891     Document Type: Article

References (24)

1. Organofluorine Compounds in Medicinal Chemistry and Biochemical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993,.
2. Sata, N.; Shibata, T.; Jitsuoka, M.; Ohno, T.; Takahashi, T.; Hirohashi, T.; Kanno, T.; Iwaasa, H.; Kanatani, A.; Fukami, T. Bioorg. Med. Chem. Lett. 2004, 14, 1761.
3. Carlsson, C.; Rosen, I.; Nilsson, E. Acta Anaesthesiol. Scand. 1993, 27, 87.
4. Kelly, T.; Bell, S.; Osashi, N.; Armstrong-Chong, J. J. Am. Chem. Soc. 1988, 110, 6471.
5. (a) Cox, R.; O'Hagan, D. J. Chem. Soc., Perkin Trans. 1 1991, 2537.
6. (b) Rigby, J.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224.
7. Williams, D.; Lowder, P.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
8. Teshima, Y.; Shin-ya, K.; Shimazu, A.; Furihota, K.; Chul, H. S.; Furihata, K.; Hayakawa, Y.; Nagai, K.; Seto, H. J. Antibiot. 1991, 44, 685.
9. Matyus, P.; Kasztreiner, E.; Diesler, E.; Behr, A.; Varga, I.; Kosary, J.; Rabloczky, G.; Jaszlits, L. Arch. Pharm. 1994, 327, 543.
10. Narusevicius, E.; Garaliene, V.; Krauze, A.; Duburs, G. Khim.-Farm. Zh. 1989, 23, 1459.
11. Nino, A.; Munoz-Caro, C.; Carbo-Dorca, R.; Girones, X. Biophys. Chem. 2003, 104, 417.
12. (a) Gerus, I. I.; Gorbunova, M. G.; Kukhar, V. P. J. Fluorine Chem. 1994, 69, 195.
13. (b) Gorbunova, M. G.; Gerus, I. I.; Kukhar, V. P. Synthesis 2000, 738.
14. Gerus, I. I.; Vdovenko, S. I.; Gorbunova, M. G.; Kukhar, V. P. Khim. Geterotsikl. Soedin. 1991, 502;
15. Chem. Abstr. 1991, 115, 1832349.
16. Kacharova, L. M.; Gerus, I. I.; Kacharov, A. D. J. Fluorine Chem. 2002, 117, 193.
17. Gerus, I. I.; Gorbunova, M. G.; Vdovenko, S. I.; Yagupolskii, Yu. L.; Kukhar, V. P. Zh. Org. Khim. 1990, 26, 1877;
18. Chem. Abstr. 1991, 115, 8196g.
19. Gerus, I. I.; Tolmachova, N. A.; Vdovenko, S. I.; Fröhlich, R.; Haufe, G. Synthesis 2005, 1269.
20. Tolmachova, N. A.; Gerus, I. I.; Vdovenko, S. I.; Essers, M.; Fröhlich, R.; Haufe, G. Eur. J. Org. Chem. 2006, 4704.
21. Volovenko, Y. M.; Nemasanyii, A. G.; Ryabokon, I. G.; Babichev, F. S. Ukr. Khim. Zh. 1988, 54, 295.
22. Shaozhong, W.; Tan, T.; Jianxin, L.; Hongwen, H. Synlett 2005, 2658.
23. Pazenok, S. V.; Gerus, I. I.; Chaika, E. A.; Yagupolskii, L. M. J. Org. Chem. USSR (Engl. Transl.) 1989, 25, 1238.
24. Hojo, R.; Masuda, M.; Okana, E. Synthesis 1990, 347.