Ring transformation of 5-acylpyrimidines and 5-acyluracils into pyrazoles with hydrazines in acidic medium

Journal of Heterocyclic Chemistry

Volumn 33, Issue 4, 1996, Pages 1003-1015

  Takagi, Kaname ^a,b   Hubert Habart, Michel ^c  

^a INSTITUT CURIE   (France)

^b KITASATO UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZOLE DERIVATIVE;

DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW;

EID: 0029819305     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330401     Document Type: Article

References (49)

1. H. C. van der Plas, Ring Transformation of Heterocycles, Vol 2, Academic Press, New York, NY, 1973, pp 119-123.
2. H. C. van der Plas and H. Jongejan, Tetrahedron Letters, 4385 (1967); ibid, Rec. Trav. Chim. Pays-Bas, 87, 1065 (1968).
3. H. C. van der Plas and H. Jongejan, Tetrahedron Letters, 4385 (1967); ibid, Rec. Trav. Chim. Pays-Bas, 87, 1065 (1968).
4. F. Baumbach, H.G. Henning and G. Hilgetag, Z. Chem., 4, 67 (1964).
5. D. J. Brown, P. W. Ford and M N. Paddon-Row, J. Chem. Soc. (C), 1452 (1968).
6. H. Wamhoff and K. Wald, Chem. Ber., 110, 1716 (1977).
7. R. Fosse, A. Hieulle and L. W. Bass, Compt. Rend Acad. Sci., 178, 811 (1924).
8. F. Lingens and H. Schneider-Bernlöhr, Liebigs Ann. Chem., 686, 134 (1965).
9. D. H. Hayes and F. Hayes-Baron, J. Chem. Soc. (C), 1528 (1967).
10. H. C. van der Plas, Heterocycles, 9, 33 (1978).
11. M. E. C. Biffin, D. J. Brown and Q. N. Porter, Tetrahedron Letters, 2029 (1967).
12. H. C. van der Plas, H. Jongejan and A. Koudijs, J. Heterocyclic Chem., 15, 485 (1978).
13. [13a] E. Mihichi in Antineoplastic and Immunosuppressive Agents Tome II, A. C. Sartorelli and D. G. Johns, eds, Springer-Verlag, Berlin, 1975, pp 766-788;
14. [b] C. W. Porter, C.V. Dave and E. Mihichi in Polyamines in Biology and Medicine, D. R. Morris and L. J. Marton, eds, Marcel Dekker Inc., 1981, pp 407-436.
15. G. Menichi, J. Naciri, B. Kokel and M. Hubert-Habart, Heterocycles. 22, 2013 (1984).
16. V. P. Arya, J. David, A. S. Grewal, S. B. Marathe and S. D. Patil, Indian J. Chem., 15B, 1129 (1977).
17. G. Menichi, M. Boutar, B. Kokel, K. Takagi and M. Hubert-Habart, J. Heterocyclic Chem., 23, 275 (1986).
18. S. C. De and P C. Rakshit, J. Indian Chem. Soc., 13, 509 (1936).
19. It has been reported that the reaction of ethoxymethylene-acetylacetone with phenylhydrazine gave 4-acetyl-5-methyl-l-phenyl-pyrazole: L. Claisen, Liebigs Ann. Chem., 295, 321 (1897).
20. 3, P. Schenone, L. Mosti and G. Menozzi, J. Heterocyclic Chem., 19, 1355 (1982); [c] R = Ph, see Ref [18].
21. 3, P. Schenone, L. Mosti and G. Menozzi, J. Heterocyclic Chem., 19, 1355 (1982); [c] R = Ph, see Ref [18].
22. 3, P. Schenone, L. Mosti and G. Menozzi, J. Heterocyclic Chem., 19, 1355 (1982); [c] R = Ph, see Ref [18].
23. K. Nagarajan, V. P. Arya and S. J. Shenoy, J. Chem. Res. (S), 166 (1986); (M), 1401 (1986).
24. K. Nagarajan, V. P. Arya and S. J. Shenoy, J. Chem. Res. (S), 166 (1986); (M), 1401 (1986).
25. J. Elquero, R. Jacquier and H. Cung N. Tien Duc, Bull. Soc. Chim. France, 3727 (1966).
26. L. G. Tensmeyer and C Ainsworth, J. Org. Chem., 31. 1878 (1966).
27. A. Cousson, F Robert and M. Hubert-Habart, Acta Cryst., C47, 395 (1991).
28. A. Cousson, B. Bachet, B. Kokel and M. Hubert-Habart, Acta Cryst., C47, 1885 (1991).
29. 3 and Ph), see Ref [19b] and [20].
30. A. Bajnati, M. Hubert-Habart, K. Takagi and H. Terada, Heterocycles, 29, 1583 (1989).
31. K. Takagi, A. Bajnati, M. Hubert-Habart and H. Terada, J. Heterocyclic Chem., 27, 1847 (1990).
32. T. J. Schwan, N. J. Milles and J. C. Butterfield, J. Heterocyclic Chem., 13, 973 (1976).
33. A. Bajnati, B. Kokel and M. Hubert-Habart, Bull. Soc. Chim. France. 318 (1987).
34. A. Cousson, F. Nextoux, B Bachet, B. Kokel and M. Hubert-Habart, Acta Cryst., C50, 286 and 289 (1994).
35. K. Takagi, A. Bajnati and M. Hubert-Habart, Heterocycles, 31, 1105 (1990); ibid, Bull. Soc. Chim. France, 127, 660 (1990).
36. K. Takagi, A. Bajnati and M. Hubert-Habart, Heterocycles, 31, 1105 (1990); ibid, Bull. Soc. Chim. France, 127, 660 (1990).
37. [32a] Z. Arnold, Collect. Czech. Chem. Commun., 26, 3051 (1961);
38. [b] Z. Arnold and J. Zemlicka, Collect. Czech. Chem. Commun., 25, 1318 (1960).
39. Synthesis of 35 by oxydation of 4-chloromethyl-1-phenylpyrazole and the formylation of 1-phenylpyrazole has been reported, I. L. Finar and G. H. Lord, J. Chem. Soc., 3314 (1957).
40. W. Bergman and T. B. Johnson, Ber., 66, 1492 (1933).
41. K. Hirota, Y. Kitade, K. Shimada, S. Senda and Y. Maki, J. Chem. Soc., Perkin Trans. 1, 1293 (1983).
42. A. Bajnati and M. Hubert-Habart, Bull. Soc. Chim. France, 540 (1988).
43. W. Bergman and T. B. Johnson, Ber., 66B, 1492 (1933).
44. K.-Y. Zee-Cheng and C. C. Cheng, J. Org. Chem., 33, 892 (1968).
45. R. H. Wiley and Y. Yamamoto, J. Org. Chem., 25, 1906 (1960).
46. R. Brossmer and D. Ziegler, Tetrahedron Letters. 5253 (1966).
47. K. Hirota, Y. Kitade, K. Shimada and S. Senda, Chem. Pharm. Bull. 29, 3760 (1981).
48. A. Bajnati, Thèse de Doctorat, Université de Paris, 1992, pp 64-72.
49. I. L. Finar and K. E. Godfrey, J. Chem. Soc., 2293 (1954).