A facile synthesis of acylhydrazines from acylbenzotriazoles

Journal of Chemical Research

Volumn , Issue 9, 2005, Pages 595-597

  Wang, Xiaoxia ^a   Yu, Hongping ^a   Xu, Peifang ^a   Zheng, Renwei ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

Acylation; Acylbenzotriazoles; Acylhydrazines; Hydrazinolysis

Indexed keywords

EID: 27144475294     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823405774308781     Document Type: Article

References (34)

1. (a) Y. Nakagawa, G. Smagghe and S. Kugimiya, Pestic. Sci., 1999, 55, 909;
2. (b) T.S. Gardner, E. Wenis and J. Lee, J. Med. Chem., 1962, 53, 503;
3. (c) C.L. Patel and H. Parekh, J. Inst. Chem., 1989, 61, 1456;
4. (d) E.J. Delikatny, W.A. Cooper, S. Brammah, N. Sathasivam and D.C. Rideout, Cancer Res., 2002, 62, 1394;
5. (e) F. Itoh, K. Kubo, H. Hosono and M. Kawamura, U.S. Pat. 6723722, 2004.
6. (a) Z.H. Chohan, H. Perrez and S. Kausar, Synth. React. Inorg. Met. Org. Chem., 2002, 32, 529;
7. (b) Z.H. Chohan, Synth. React. Inorg. Met. Org. Chem., 2001, 31, 1;
8. (c) Z.H. Chohan, M.A. Faroog and M.S. Iqbal, Metal Based Drugs, 2000, 7, 133;
9. (d) P. Molina, A. Tarraga and J.L. Lopez, J. Organomet. Chem., 1999, 584, 147.
10. V.K. Jadhav, P.P. Wadagaonkar and M.M. Salunkhe, J. Chin. Chem. Soc., 1998, 45, 831 and references cited therein.
11. For example: (a) R. Vanderesse, L. David, V. Grand and M. Marraud, Tetrahedron Lett., 1997, 38, 2669;
12. (b) Z. Wang, R.T. Skerlji and G.J. Bridger, Tetrahedron Lett., 1999, 40, 3543;
13. (c) L. Grehn and U. Ragnarsson, Tetrahedron, 1999, 55, 4843;
14. (d) R.L. Hinman, J. Am. Chem. Soc., 1957, 79, 414;
15. (e) R.L. Hinman and M.C. Flores, J. Org. Chem., 1959, 24, 660;
16. (f) N. Brosse, M.-F. Pinto and Brigitte Jamart-Grégoire, J. Org. Chem., 2000, 65, 4370.
17. A.F. Hegarty, The Chemistry of Hydrazo, Azo and Azoxy Groups in The Chemistry of Functional Groups, part 2, Chap. 16, Ed. S. Patai, Wiley and Sons, 1975.
18. R.L. Hinman and D. Fulton, J. Am. Chem. Soc., 1958, 80, 1895.
19. M.A.P.J. Hacking, F.V. Rantwijk and R.A. Sheldon, J. Mol. Catal. B: Enzym., 2000, 9, 183.
20. (a) A.R. Katritzky, A.A. Shestopalov and K. Suzuki, Synthesis, 2004, 1806;
21. (b) B. Castro, J.R. Dormoy, G. Evin and C. Selve, Tetrehedron Lett., 1975, 16, 1219;
22. (c) K. Barlos, D. Papaioannou and D. Theodoropoulos, Int. J. Peptide Protein Res., 1984, 23, 300;
23. (d) A.R. Katritzky, H.X. Chang and B. Yang, Synthesis, 1995, 503;
24. (e) A.R. Katritzky, B. Yang and D. Semenzin, J. Org. Chem., 1997, 62, 726;
25. (f) A.R. Katritzky, J.R. Levell and D.P.M. Pleynet, Synthesis, 1998, 153.
26. (a) A.R. Katritzky, H.Y. He and K. Suzuki, J. Org. Chem., 2000, 65, 8210;
27. (b) A.R. Katritzky, N. Kirichenko and B.V. Rogovoy, Synthesis, 2003, 2777;
28. (c) A.R. Katritzky, M. Wang and S. Zhang, Arkivoc 2001, iX, 19.
29. A.L. Baumstark and P.C. Basquez, J. Org. Chem., 1983, 48, 65.
30. J.P. Li, S.Q. Yu, G.R. Qu and Y.L. Wang, J. Chin. Chem. Soc., 2004, 51, 835.
31. A.F.M. Fahmy and H.A. Fadel, Ind. J. Chem., 1973, 11, 725.
32. R.A. Rebelo, M.C. Rezende, F. Nome and C. Zucco, Synth. Commun., 1987, 17, 1741.
33. K. Issleib and O. Loew, Z. Anorg. Allg. Chem., 1966, 346, 241. (Beilstein (2004/ 02): Substances:Q07 hit 1, BRN 1821484).
34. A.S. Endler and E.I. Becker, Org. Synth. Collect., 1963, 4, 657.