Practical synthesis of 1,3-diaryl-5-alkylpyrazoles by a highly regioselective N-arylation of 3,5-disubstituted pyrazoles with 4- fluoronitrobenzene

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5321-5324

  Wang, Xiao Jun ^a   Tan, Jonathan ^a   Grozinger, Karl ^a   Betageri, Raj ^a   Kirrane, Tom ^a   Proudfoot, John R ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIARYL 5 ALKYLPYRAZOLE DERIVATIVE; NITROBENZENE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; POLYMERIZATION; SYNTHESIS;

EID: 0034622308     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00849-2     Document Type: Article

References (13)

1. Kost, A. N.; Grandberg, I. I. In Advances in Heterocyclic Chemistry; Kartrizky, A. R.; Boulton, A. J., Ed.; Academic Press: New York, 1966; Vol. 6, 347.
2. For examples, see: (a) Murray, W.; Wachter, D. B.; Barton, D.; Forero-Kelly, Y. Synthesis 1991, 18-20; (b) Kashima, C.; Harada, H.; Kita, I.; Fukuchi, I.; Hosomi, A. Synthesis 1994, 61-65. (c) Luo, Y.; Potvin, P. G. J. Org. Chem. 1994, 59, 1761-1765.
3. For examples, see: (a) Murray, W.; Wachter, D. B.; Barton, D.; Forero-Kelly, Y. Synthesis 1991, 18-20; (b) Kashima, C.; Harada, H.; Kita, I.; Fukuchi, I.; Hosomi, A. Synthesis 1994, 61-65. (c) Luo, Y.; Potvin, P. G. J. Org. Chem. 1994, 59, 1761-1765.
4. For examples, see: (a) Murray, W.; Wachter, D. B.; Barton, D.; Forero-Kelly, Y. Synthesis 1991, 18-20; (b) Kashima, C.; Harada, H.; Kita, I.; Fukuchi, I.; Hosomi, A. Synthesis 1994, 61-65. (c) Luo, Y.; Potvin, P. G. J. Org. Chem. 1994, 59, 1761-1765.
5. Elguero, J. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W., Ed.; Pergamon Press: Oxford, 1984; Vol. 5, 167.
6. 2: C, 69.61; H, 5.15; N, 14.32. Found: C, 69.65; H, 5.19; N, 14.43.
7. (a) Sugaya, T.; Mimury, Y.; Ikuta, M.; Mimury, T.; Kasai, M.; Tomioka, S. Synthesis 1994, 73-76.
8. (b) Cerrada, M. L.; Elguero, J.; De La Fuente, J.; Pardo, C.; Ramos, M. Synth. Commun. 1993, 23, 1947-1952.
9. (c) Park, K. H.; Cho, S. Y.; Yum, E. K.; Yu, C. M.; Hwang, K. J. Bull. Korean Chem. Soc. 1995, 16, 799-801.
10. (d) Finar, I. L.; Hurlock, R. J. J. Chem. Soc. 1957, 3024-3026.
11. Wiley, R. H.; Hexaner, P. E. Org. Synth. Coll. Vol. IV 1963, 351-353.
12. Kashima, C.; Fukuchi, I.; Takahashi, K.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8305-8308.
13. 2 if not isolated from the N-arylation.