The structure of 4-benzoyl-5-methyl-2-phenylpyrazol-3-one oxime and its methyl derivatives

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1209-1219

  Holzer, Wolfgang ^a   Hahn, Katharina ^a   Brehmer, Thomas ^a   Claramunt, Rosa M ^b   Pérez Torralba, Marta ^b  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

Density functional calculations; NMR spectroscopy; Oximes; Tautomerism; X ray diffraction

Indexed keywords

(5 METHOXY 3 METHYL 1 PHENYL 1H PYRAZOL 4 YL)(PHENYL)METHANONE O METHYLOXIME; (5 METHOXY 3 METHYL 1 PHENYL 1H PYRAZOL 4 YL)(PHENYL)METHANONE OXIME; 1 (5 METHOXY 3 METHYL 1 PHENYL 1H PYRAZOL 4 YL)ETHANONE OXIME; 1,2 DIHYDRO 4 [(HYDROXYIMINO)(PHENYL)METHYL] 1,5 DIMETHYL 2 PHENYL 3H PYRAZOL 3 ONE; 1,2 DIHYDRO 4 [(METHOXYMINO)(PHENYL)METHYL] 1,5 DIMETHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(HYDROXYAMINO)(PHENYL)METHYLENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(N HYDROXY N METHYLAMINO)(PHENYL)METHYLENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(N METHOXY N METHYLAMINO)PHENYLMETHYLENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 4 BENZOYL 5 METHYL 2 PHENYLPYRAZOL 3 ON OXIME; 4 [(METHOXYAMINO)(PHENYL)METHYLENE] 5 METHYL 2 PHENYL 2,4 DIHYDRO 3H PYRAZOL 3 ONE; BENZENE DERIVATIVE; DICHLOROMETHANE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID STATE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037391624     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390175     Document Type: Article

References (41)

1. J. Elguero, C. Marzin, A. R. Katritzky, P. Linda, in Advances in Heterocyclic Chemistry: The Tautomerism of Heterocycles, Suppl. 1, Academic Press, New York, 1976, pp. 313-336, and references cited therein.
2. [2a] J. Elguero, in Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives, vol. 5 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984, pp. 167-303.
3. [2b] J. Elguero, in Comprehensive Heterocyclic Chemistry II: Pyrazoles, vol. 3 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, pp. 1-75.
4. M. J. O'Connell, C. G. Ramsay, P. J. Steel, Aust. J Chem. 1985, 38, 401-409, and references cited therein.
5. L. N. Kurkovskaya, N. N. Shapet'ko, A. S. Vitvitskaya, I. Y. Kvitko, J Org. Chem. USSR (Engl. Transl.) 1977, 13, 1618-1625 (Original paper: Zh. Org. Khim. 1977, 13, 1750-1757).
6. W. Holzer, K. Mereiter, B. Plagens, Heterocycles 1999, 50, 799-818.
7. A. B. Uzoukwu, S. S. Al-Juaid, P. B. Hitchcock, J. D. Smith, Polyhedron 1993, 12, 2719-2724.
8. Y. Akama, M. Shiro, T. Ueda, M. Kajitani, Acta Crystallogr., Sect. C 1995, 51, 1310-1314, and references cited therein.
9. J. A. M. Guard, P. J. Steel, Aust. J. Chem. 1994, 47, 1453-1459.
10. Y. Akama, A. Tong, Microchem. J. 1996, 53, 34-41.
11. Presented at the 8th Blue Danube Symposium on Heterocyclic Chemistry, Bled, September 2000, poster No. PO 30; W. Holzer, T. Brehmer, D. Guggi, M. Perez-Torralba, R. M. Claramunt, manuscript in preparation.
12. Presented at the 8th Blue Danube Symposium on Heterocyclic Chemistry, Bled, September 2000, poster No. PO 30; W. Holzer, T. Brehmer, D. Guggi, M. Perez-Torralba, R. M. Claramunt, manuscript in preparation.
13. A. S. Sarenko, I. Y. Kvitko, L. S. Éfros, Chem. Heterocyclic Comp. (Engl. Transl.) 1972, 722-727 (Original paper: Khim. Geterotsikl. Soedin. 1972, 799-804).
14. W. Holzer, B. Plagens, Sci. Pharm. 1996, 64, 455-462.
15. A. Michaelis, F. Engelhardt, Ber. Dtsch. Chem. Ges. 1908, 41, 2668-2676.
16. L. Hennig, G. Mann, Z. Chem. 1988, 28, 364-365.
17. A. K. Rana, J. R. Shah, Indian J. Chem. 1981, 20A, 142-144.
18. L. Avar, K. Hofer (Sandoz), Ger. Offen. DE 2529052, 1976, Chem. Abstr. 1976, 85, 6648.
19. S. L. Patt, J. N. Shoolery, J. Magn. Reson. 1982, 46, 535-539.
20. D. Neuhaus, M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH Publishers, New York, 1989.
21. D. G. Davis, A. Bax, J. Am. Chem. Soc. 1985, 107, 7197-7198.
22. A. Bax, S. Subramanian, J. Magn. Reson. 1986, 67, 565-569.
23. S. K. Sarkar, A. Bax, J. Magn. Reson. 1985, 62, 109-112.
24. A. Bax, J. Magn. Reson. 1984, 57, 314-318.
25. 13C NMR spectrum was not possible, but a satisfactory broad-band decoupled spectrum emerged after performing 16000 scans.
26. G. E. Hawkes, K. Herwig, J. D. Roberts, J. Org. Chem. 1974, 39, 1017-1028.
27. G. Heinisch, W. Holzer, Tetrahedron Lett. 1990, 31, 3109-3112.
28. G. Heinisch, W. Holzer, Monatsh. Chem. 1990, 121, 837-846.
29. G. Heinisch, W. Holzer, Collect. Czech. Chem. Communn. 1991, 56, 2251-2257.
30. W. Freyer, J. Prakt. Chem. 1977, 319, 911-918.
31. H.-H. Otto, H. Schmelz, Monatsh. Chem. 1980, 111, 53-61.
32. U. Kölle, B. Kolb, A. Mannschreck, Chem. Ber. 1980, 113, 2545-2565.
33. X.-C. Tang, D.-Z. Jia, K. Liang, X.-G. Zhang, X. Xia, Z.-Y. Zhou, J. Phtochem. Photobiol. A 2000, 134, 23-29.
34. H. Kraudelt, U. Schilde, H. Hefele, E. Ludwig, E. Uhlemann, Z. Naturforsch., Teil B 1996, 51b, 1240-1244.
35. TITAN v1.0.5, Wavefunction Inc., Irvine, CA 92612, USA, 1999.
36. SIR92 - A program for crystal structure solution: A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J. Appl. Crystallogr. 1993, 26, 343-350.
37. SHELX97 - Programs for Crystal Structure Analysis (Release 97-2), G. M. Sheldrick, Institut für Anorganische Chemie der Universität Göttingen, Tammanstrasse 4, 3400 Göttingen, Germany, 1998.
38. [36a] A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, C34.
39. [3b] A. L. Spek, PLATON - A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1998.
40. DIAMOND 2.1a - Visual crystal structure information systems, K. Brandenburg, 1999.
41. WINGX v1.63. 01 - System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data: L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.