TBPA+{radical dot} mediated aromatization of 1,3,5-trisubstituted pyrazolines

Chinese Chemical Letters

Volumn 19, Issue 9, 2008, Pages 1013-1016

  Su, Gang ^a   Wu, Wen Tao ^a   Wang, Jian Tao ^a   Wu, Long Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Aromatization; Cation radical; Pyrazole; Pyrazoline

Indexed keywords

EID: 47049085667     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2008.06.003     Document Type: Article

References (26)

1. Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. (1998), Addison-Wesley Longman, England
2. Lednicer D. Strategies for Organic Drugs Synthesis and Design (1998), Wiley & Sons, New York (Chapters 8 and 9)
3. Takabata E., Kodama R., Tanaka Y., Dohmori R., Tachizawa H., and Naito T. Chem. Pharm. Bull. 16 (1979) 1900
4. Parmar S.S., Pandey B.R., Dwivedi C., and Harbison R.D. J. Pharm. Sci. 63 (1974) 1152
5. Soni N., Pande K., Kalsi R., Gupta T.K., Parmer S.S., and Barthwal J.P. Res. Commun. Chem. Pathol. Pharmacol. 56 (1987) 129
6. Shenoy G.G., Bhat A.R., and Kotian M. Indian J. Heterocycl. Chem. 10 (2001) 197
7. Polevoi L.G. Chem. Abstr. 65 (1966) 19147
8. Harinadha B.V., Sridevi C.H., Joseph A., and Srinivasan K.K. Indian J. Pharm. Sci. 69 (2007) 470
9. Yun Z., Zhou W.G., Jiang Q., and Xie M.G. Chin. Chem. Lett. 8 (1999) 679
10. Gladstone W.A.F., and Norman R.O.C. J. Chem. Soc. Chem. Commun. (1966) 1536
11. Franck-Neumann M., and Miesch M. Tetrahedron Lett. 23 (1982) 1409
12. Zolfigol M.A. Tetrahedron Lett. 47 (2006) 833
13. Sabitha G., Reddy G.S., Reddy Ch.S., Fatima N., and Yadav J.S. Synthesis 8 (2003) 1267
14. Singh S.P., Kumar D., Prakash O., and Kapoor R.P. Synth. Commun. 27 (1997) 2683
15. Nakamichi N., Kawashita Y., and Hayashi M. Org. Lett. 4 (2002) 3955
16. Nakamichi N., Kawashita Y., and Hayashi M. Synthesis 7 (2004) 1015
17. Han B., Liu Z.G., Liu Q., Yang L., Liu Z.L., and Yu W. Tetrahedron 62 (2006) 2492
18. Chai L.Z., Zhao Y.K., Sheng Q.J., and Liu Z.Q. Tetrahedron Lett. 47 (2006) 9283
19. Dapperheld S., Steckhan E., Brinkhaus K.-H.G., and Esch T. Chem. Ber. 124 (1991) 2557
20. Bell F.A., Ledwith A., and Sherrington D.C. J. Chem. Soc. (1969) 2719
21. Schmidt W., and Steckhan F. Chem. Ber. 113 (1980) 577
22. 2, the residue was purified by column chromatography on silica gel with a mobile phase of n-hexane-ethyl acetate (30:1, v/v), affording 270 mg (91% yield) of 1,3,5-triphenyl pyrazole (2a).
23. 3, δ ppm): 105.1 (C4 of the pyrazole ring), 125.2 (2C), 125.7, 127.3 (2C), 127.9 (2C), 128.2, 128.4, 128.6 (2C), 128.7 (2C), 128.8 (2C), 130.4, 132.9, 140.0, 144.3, 151.8; EI-MS (70 eV) m/z (%): 296 (78.7), 267 (6.1), 192 (10.4),165 (22.5), 89 (19.3), 77 (100.0), 63 (18.2), 51 (47.4), 39 (12.2).
24. Takahashi Y., Miyashi T., and Mukai T. J. Am. Chem. Soc. 105 (1983) 6511
25. Schaap A.P., Prasad G., and Gagnon S.D. Tetrahedron Lett. 24 (1983) 3047
26. Olson P.D., and Varner J.E. Plant J. 4 (1993) 887