Synthesis and NMR spectroscopic investigations with 3-amino-, 3-hydroxy-, and 3-methoxy-4-acyl-1-phenyl-2-pyrazolin-5-ones

Heterocycles

Volumn 63, Issue 6, 2004, Pages 1311-1334

  Holzer, Wolfgang ^a   Hallak, Linda ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 4 ACYL 1 PHENYL 2 PYRAZOLIN 5 ONE DERIVATIVE; 3 HYDROXY 4 ACYL 1 PHENYL 2 PYRAZOLIN 5 ONE DERIVATIVE; 3 METHOXY 4 ACYL 1 PHENYL 2 PYRAZOLIN 5 ONE DERIVATIVE; 4 DIMETHYLAMINOMETHYLENE; 4 HYDROXYIMINO DERIVATIVE; ACETAL DERIVATIVE; CALCIUM HYDROXIDE; CARBOXYLIC ACID; CHLORIDE; DIOXANE; METHYLAMINE; N,N DIMETHYLFORMAMIDE; N,N DIMETHYLFORMAMIDE DIETHYL ACETAL; NITROUS ACID; OXIME; TETRACYANOETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; NITROGEN NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 2942623682     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-10046     Document Type: Article

References (56)

1. J. Elguero, C. Marzin, and A. R. Katritzky, 'Advances in Heterocyclic Chemistry: The Tautomerism of Heterocycles', Suppl. 1, Academic Press, New York, 1976, pp. 313-336.
2. 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, pp. 167-303.
3. V. I. Minkin, A. D. Gamovskii, J. Elguero, A. R. Katritzky, and O. V. Denisko, 'The tautomerism of heterocycles: Five-membered rings with two or more heteroatoms', Advances in Heterocyclic Chemistry, 2000, 76, 157-323; and references cited therein.
4. H. Dorn, J. Prakt. Chem., 1973, 315, 382.
5. L. N. Kurkovskaya, N. N. Shapet'ko, A. S. Vitvitskaya, and A. Y. Kvitko, J. Org. Chem. USSR (Engl. Transl.), 1977, 13, 1618; original paper: Zh. Org. Khim., 1977, 13, 1750.
6. L. N. Kurkovskaya, N. N. Shapet'ko, A. S. Vitvitskaya, and A. Y. Kvitko, J. Org. Chem. USSR (Engl. Transl.), 1977, 13, 1618; original paper: Zh. Org. Khim., 1977, 13, 1750.
7. A. R. Katritzky, M. Karelson, and P. A. Harris, Heterocycles, 1991, 32, 329.
8. E. Kleinpeter and A. Koch, J. Phys. Org. Chem., 2001, 14, 566.
9. M. J. O'Connell, C. G. Ramsay, and P. J. Steel, Aust. J. Chem., 1985, 38, 401; and references cited therein.
10. A. B. Uzoukwu, S. S. Al-Juaid, P. B. Hitchcock, and J. D. Smith, Polyhedron, 1993, 12, 2719.
11. Y. Akama, M. Shiro, T. Ueda, and M. Kajitani, Acta Cryst., 1995, C51, 1310; and references cited therein.
12. Y. Akama and A. Tong, Microchem. J., 1996, 53, 34.
13. J. A. M. Guard and P. J. Steel, Aust. J. Chem., 1994, 47, 1453.
14. W. Holzer, K. Mereiter, and B. Plagens, Heterocycles, 1999, 50, 799.
15. W. Holzer, K. Hahn, T. Brehmer, R. M. Claramunt, and M. Pérez-Torralba, Eur. J. Org. Chem., 2003, 1209.
16. W. Holzer, R. M. Claramunt, M. Pérez-Torralba, D. Guggi, and T. H. Brehmer, J. Org. Chem., 2003, 68, 7943.
17. B. S. Jensen, Acta Chem. Scand., 1959, 13, 1668.
18. O. N. Kataeva, A. T. Gubaidullin, I. A. Litvinov, O. A. Lodochnikova, L. R. Islamov, A. I. Movchan, and G. A. Chmutova, J. Mol. Struct., 2002, 610, 175.
19. J. Fu and S. J. Shuttleworth, Tetrahedron Lett., 2003, 44, 3843.
20. Y. Lu, J. Shen, H. Yang, X. Cui, J. Pang, and S. Cheng, Huaxue Shiji, 1993, 15, 83 (Chem. Abstr., 1993, 119, 139167).
21. Y. Lu, J. Shen, H. Yang, X. Cui, J. Pang, and S. Cheng, Huaxue Shiji, 1993, 15, 83 (Chem. Abstr., 1993, 119, 139167).
22. Y. Lu, H. Yang, J. Shen, X. Cui, J. Pang, and M. Cai, Huaxue Tongbao, 1993, 39 (Chem. Abstr., 1993, 119, 28049).
23. Y. Lu, H. Yang, J. Shen, X. Cui, J. Pang, and M. Cai, Huaxue Tongbao, 1993, 39 (Chem. Abstr., 1993, 119, 28049).
24. A. Molinari, A. Oliva, and L. Sanchez, Bol. Soc. Chil. Quim., 1996, 41, 423 (Chem. Abstr., 1997, 126, 171515).
25. A. Molinari, A. Oliva, and L. Sanchez, Bol. Soc. Chil. Quim., 1996, 41, 423 (Chem. Abstr., 1997, 126, 171515).
26. H. Junek, M. Klade, H. Sterk, and W. Fabian, Monatsh. Chem., 1988, 119, 993.
27. K. Kirschke, 'Houben-Weyl: Methoden der Organischen Chemie', Vol. E8b, ed. by E. Schaumann, Thieme Verlag, Stuttgart - New York, 1994, p. 596.
28. L. Knorr, Ann. Chem., 1887, 238, 137.
29. J. Bartulin, J. Belmar, H. Gallardo, and G. Leon, J. Heterocycl. Chem., 1994, 31, 561.
30. W. Hänsel, Arch. Pharm. (Weinheim), 1976, 309, 900.
31. D. Neuhaus and M. P. Williamson, 'The Nuclear Overhauser Effect in Structural and Conformational Analysis', VCH, New York, 1989, pp. 211-252.
32. K. E. Köver and G. Batta, Prog. NMR Spectrosc., 1987, 19, 223.
33. C. Szantay Jr., Z. Csepregi, P. Aranyosi, I. Rusznak, L. Töke, and A. Vig, Magn. Reson. Chem., 1997, 35, 30.
34. D. G. Davis and A. Bax, J. Am. Chem. Soc., 1985, 107, 7197.
35. S. L. Patt and J. N. Shoolery, J. Magn. Reson., 1982, 46, 535.
36. A. Bax and S. Subramanian, J. Magn. Reson., 1986, 67, 565.
37. A. Bax and M. F. Summers, J. Am. Chem. Soc., 1986, 108, 2093.
38. S. K. Sarkar and A. Bax, J. Magn. Reson., 1985, 62, 109.
39. A. Bax, J. Magn. Reson., 1984, 57, 314.
40. T. Jippo, O. Kamo, and N. Nagayama, J. Magn. Reson., 1986, 66, 344.
41. G. A. Morris and R. Freeman, J. Am. Chem. Soc., 1979, 101, 760.
42. D. P. Burum and R. R. Ernst, J. Magn. Reson., 1980, 39, 163.
43. L. E. Kay, P. Keifer, and T. Saarinen, J. Am. Chem. Soc., 1992, 114, 10663.
44. A. G. Palmer III, J. Cavanagh, P. E. Wright, and M. Rance, J. Magn. Reson., 1991, 93, 151.
45. J. Schleucher, M. Schwendinger, M. Sattler, P. Schmidt, O. Schedletzky, S. J. Glaser, O. W. Sorensen, and C. Griesinger, J. Biomol. NMR, 1994, 4, 301.
46. W. Willker, D. Leibfritz, R. Kerssebaum, and W. Bermel, Magn. Reson. Chem., 1993, 31, 287.
47. J. Frigola, A. Colombo, J. Pares, L. Martinez, R. Sagarra, and R. Roser, Eur. J. Med. Chem., 1989, 24, 435.
48. W. Holzer and I. Krca, Heterocycles, 2003, 60, 2323.
49. U. Kölle, B. Kolb, and A. Mannschreck, Chem. Ber., 1980, 113, 2545.
50. W. Freyer, J. Prakt. Chem., 1977, 319, 911.
51. H.-H. Otto and H. Schmelz, Monatsh. Chem., 1980, 111, 53.
52. G. E. Hawkes, K. Herwig, and J. D. Roberts, J. Org. Chem., 1974, 39, 1017.
53. G. C. Levy and G. L. Nelson, J. Am. Chem. Soc., 1972, 94, 4897.
54. A. Weissberger and H. D. Porter, J. Am. Chem. Soc., 1943, 65, 52.
55. A. Molinari and A. Oliva, J. Heterocycl. Chem., 1996, 33, 479.
56. A. Maquestiau, Y. Van Haverbeke, and J. J. Van den Eynde, Bull. Soc. Chim. Belg., 1981, 90, 963.