Hypervalent iodine oxidation of 1-phenyl-3-arylpyrazole-4-carboxaldehyde oximes: A facile and efficient synthesis of new 3,4-bis(1-phenyl-3- arylpyrazolyl)-1,2,5-oxadiazole-N-oxides

Arkivoc

Volumn 2007, Issue 13, 2007, Pages 28-33

  Prakash, Om ^a   Pannu, Kamaljeet ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

3,4 Bis(1 phenyl 3 arylpyrazolyl) 1,2,5 oxadiazole N oxide; Hypervalent iodine reagents; IBD; Oxidation; Pyrazole 4 carboxaldehyde oxime

Indexed keywords

EID: 33947363808     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.d04     Document Type: Article

References (30)

1. Recent reviews on hypervalent iodine reagents: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
2. (b) Ladzita, U.; Zhdankin, V. V. Arkivoc 2006, 9, 26.
3. (c) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
4. (d) Wirth, T. Top. Curr. Chem. 2003, 224.
5. (a) Moriarty, R. M.; Chany II, C. J.; Kosmeder II, J. W. In Encyclopedia of Reagents in Organic Synthesis Paquette, L. A, Ed., Wiley: Chichester, 1995, Vol 2, pp1479.
6. (b) Prakash, O.; Singh, S. P. Aldrichimica Acta 1994, 27, 15.
7. (c) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377.
8. (a) Koser, G. F. Aldrichimica Acta 2001, 34, 89.
9. (b) Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409.
10. (c) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365.
11. (a) Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347.
12. (b) Ochiai, M.; Utika, T.; Iwaki, S.; Nagao, Y.; Fujita, E. J. Org. Chem 1989, 54, 4832.
13. (c) Zhdankin, V. V.; Mullikin, M.; Tykwinski, R.; Berglund, B.; Caple, R.; Zefirov, N. S.; Kozmin, A. S. J. Org. Chem. 1989, 54, 2605.
14. (a) Moriarty, R. M.; Prakash, O.; Vavilikolanu, P. R. Synth. Commun. 1986, 16, 1247.
15. (b) Prakash, O.; Pahuja, S.; Sawhney, S. N. Indian J. Chem. 1989, 26B, 73.
16. (a) Barton, D. H. R.; Jasberenyi, J. Cs.; Liu, W.; Shinada, T. Tetrahedron 1996, 52 (47);
17. (b) Prakash, O.; Gujral, H. K.; Rani, N.; Singh, S. P. Synth. Commun. 2000, 30, 417.
18. (c) Pundeer, R.; Chaudhri, V.; Kinger, M.; Prakash, O. Indian J Chem, Sect. B (In press).
19. (a) Prakash O.; Sharma, V.; Sadana, A. J Chem Res (S) 1996, 100.
20. (b) Wutz, P. G. M.; Goble, M. P. Org. Lett. 2000, 2, 2139.
21. Grundman, C.; Dean, J. M. J. Org. Chem. 1965, 30, 2809.
22. Just, G.; Dahl, K. Tetrahedron Lett. 1968, 24, 5251.
23. Grundman, C.; Richter, R. J. Org. Chem. 1968, 33, 476.
24. Hassner, A.; Lokanatha R. K. M. Synthesis 1989, 57.
25. Kim, J. N.; Ryu, K. R. Synth. Commun. 1990, 20, 1373.
26. Radhakrishnan, A. S.; Sivaprakash, K.; Singh, B. B. Synth. Commun. 1991, 21, 1625.
27. (a) Paton, R. M. Comprehensive Heterocyclic Chemistry II; 1996, Vol. 4, 229.
28. (b) Baker, K. W. J.; Gibb, A.; March, A. R.; Paton, R. M. Tetrahedron Lett. 2001, 42, 4065.
29. Prakash, O.; Pannu, K; Kaur, H; Naithani, R. Synth. Commun. 2006, 23, 5479.
30. 13C NMR could be obtained only for representative example 4a because of insolubility problem of products 4b-f.