Regioselective reaction of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates and phenylhydrazine: Synthesis of trifluoromethyl substituted pyrazole and 1,2,4-triazine derivatives

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 663-666

  Kawase, Masami ^a   Koiwai, Hiromi ^a   Yamano, Akihito ^b   Miyamae, Hiroshi ^a  

^a JOSAI UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; PHENYLHYDRAZINE; PYRAZOLE DERIVATIVE; PYRAZOLONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032509941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10712-2     Document Type: Article

References (11)

1. 1. Kawase, M. J. Chem. Soc., Chem. Commun., 1994, 2101.
2. 2. Kawase, M.; Saito, S.; Kurihara, T. Heterocycles, 1995, 41, 1617.
3. 3. Elguero, J. Comprehensive Heterocyclic Chemistry; Potts, K. T. Ed.; Pergamon Press: Oxford. 1984; vol. 5; pp. 167-303.
4. 4. Bravo, P.; Diliddo, D.; Resnati, G.Tetrahedron, 1994, 50, 8827; Shawali, A. S.; Hassaneen, H. M. Tetrahedron, 1973, 29, 121.
5. 4. Bravo, P.; Diliddo, D.; Resnati, G.Tetrahedron, 1994, 50, 8827; Shawali, A. S.; Hassaneen, H. M. Tetrahedron, 1973, 29, 121.
6. 5. Potts, K. T. 1,3 -Dipolar Cycloaddition Chemistry; Padwa, A. Ed.; Wiley-Interscience: New York. 1984; vol. 2; pp. 1-82.
7. CF=260.0), 121.93(C), 125.33 (CH), 128.37 (CH), 129.09 (CH), 139.05 (C), 154.79 (CO).
8. W=0.025, S=8.451). Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
9. 13C NMR chemical shifts of 3-trifluoromethyl-5-hydroxy-and 5-trifluoromethyl-3-hydroxypyrazoles are described in the following literature: Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J. Heterocyclic Chem., 1990, 27, 243.
10. 9. Kees, K. L.; Fitzgerald, Jr. J. J.; Steiner, K. E.; Mattes, J. F.; Mihan, B.; Tosi, T.; Modoro, D.; McCaleb, M. L. J. Med. Chem., 1996, 39, 3920 and references therein.
11. 10. Kamitori, Y.; Hojo, M.; Masuda, R.; Sukegawa, M.; Hayashi, K.; Kouzeki, K. Heterocycles, 1994, 39, 155 and references therein.