Transformation of N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)benzamide with hydrazines in the presence of an acidic catalyst

Heterocycles

Volumn 61, Issue , 2003, Pages 105-112

  Vraničar, Lidija ^a   Polanc, Slovenko ^a   Kočevar, Marijan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZINE DERIVATIVE; N (5 ACETYL 6 METHYL 2 OXO 2H PYRAN 3 YL)BENZAMIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS;

EID: 17544397283     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s1     Document Type: Article

References (26)

1. (a) J. D. Hepworth, Comprehensive Heterocyclic Chemistry: Pyrans and Fused Pyrans: (iii) Synthesis and Applications, Vol. 3, ed. by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, p. 737;
2. (b) G. P. Ellis, Comprehensive Heterocyclic Chemistry: Pyrans and Fused Pyrans: (ii) Reactivity, Vol. 3, ed. by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, p. 647;
3. (c) M. Kočevar, Chem. Listy, 1997, 91, 610 (Chem. Abstr., 1997, 127, 318834f).
4. (c) M. Kočevar, Chem. Listy, 1997, 91, 610 (Chem. Abstr., 1997, 127, 318834f).
5. (a) J. Elguero, Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives, Vol. 5, ed. by A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, p. 167;
6. (b) J. Elguero, Comprehensive Heterocyclic Chemistry II: Pyrazoles, Vol. 3, ed. by A. R. Katritzky, C. W. Rees, and E. F. W. Scriven, Pergamon Press, Oxford, 1996, p. 1.
7. (a) P. Trebše, S. Polanc, M. Koševar, T. Šolmajer, and S. Golić Grdadolnik, Tetrahedron, 1997, 53, 1383;
8. (b) L. Vraničar, S. Polanc, and M. Kočevar, Tetrahedron, 1999, 55, 271.
9. (a) L. Vraničar, A. Meden, S. Polanc, and M. Kočevar, J. Chem. Soc., Perkin Trans. 1, 2002, 675;
10. (b) L. Vraničar, F. Požgan, S. Polanc, and M. Kočevar, Amino Acids, in press.
11. (a) A. Černigoj-Marzi, S. Polanc, and M. Kočevar, J. Heterocycl. Chem., 1997, 34, 1753;
12. (b) P. Trebše, B. Recelj, M. Kočevar, and S. Polanc, J. Heterocycl. Chem., 1997, 34, 1247;
13. (c) P. Trebše, B. Recelj, T. Lukanc, S. Golič Grdadolnik, A. Petrič, B. Verček, T. Solmajer, S. Polanc, and M. Kočevar, Synth. Commun., 1997, 27, 2637;
14. (d) M. Ješelnik, R. S. Varma, S. Polanc, and M. Kočevar, Chem. Commun., 2001, 1716;
15. (e) M. Ješelnik, R. S. Varma, S. Polanc, and M. Kočevar, Green Chemistry, 2002, 4, 35;
16. (f) S. Golič Grdadolnik, P. Trebše, M. Koševar, and T. Šolmajer, J. Chem. Inf. Comput. Sci., 1997, 37, 489;
17. (g) P. Trebše, L. Vraničar, I. Mušič, S. Polanc, W. C. Stevens, and M. Kočevar, Heterocycles, 2000, 53, 1111.
18. P. Trebše, S. Polanc, and M. Kočevar, Heterocycles, 2003, 59, 129.
19. Two tautomeric forms (a and b) of the intermediate (6) have been postulated for the formation of α,β-didehydro-α-amino acid derivatives (4).4 The intermediate (6) can be transformed into products ((E)-4) via the tautomeric form (6a) or eventually via 6b (probably in addition to Z-4), but Z-4 can only be formed via intermediate (6b), which possesses a single bond
20. G. Hajós, Z. Riedl, and G. Kollenz, Eur. J. Org. Chem., 2001, 3405.
21. V. Kepe, M. Kočevar, S. Polanc, B. Verček, and M. Tišler, Tetrahedron, 1990, 46, 2081.
22. (a) N. Takahayashi, J. Pharm. Soc. Japan, 1955, 75, 778 (Chem. Abstr., 1956, 50, 4970c);
23. (a) N. Takahayashi, J. Pharm. Soc. Japan, 1955, 75, 778 (Chem. Abstr., 1956, 50, 4970c);
24. (b) N. Takahayashi, J. Pharm. Soc. Japan, 1956, 76, 765 (Chem. Abstr., 1957, 51, 1192d);
25. (b) N. Takahayashi, J. Pharm. Soc. Japan, 1956, 76, 765 (Chem. Abstr., 1957, 51, 1192d);
26. (c) A. Pollak and M. Tišler, Tetrahedron, 1966, 22, 2073.