On the tautomerism of pyrazolones: The geminal 2J[pyrazole C-4,H-3(5)] spin coupling constant as a diagnostic tool

Tetrahedron

Volumn 60, Issue 32, 2004, Pages 6791-6805

  Holzer, Wolfgang ^a   Kautsch, Constanze ^a   Laggner, Christian ^a   Claramunt, Rosa M ^b   Pérez Torralba, Marta ^b   Alkorta, Ibon ^c   Elguero, José ^c  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

DFT calculations; Methylation; NOE difference spectroscopy; Pyrazolones; Spin coupling constants; Tautomerism

Indexed keywords

BENZENE; DIMETHYL SULFOXIDE; KETONE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRAZOLONE DERIVATIVE;

ACCELERATION; AQUEOUS SOLUTION; ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHEMICAL REACTION; EQUILIBRIUM CONSTANT; INFRARED SPECTROSCOPY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RACEMIC MIXTURE; TAUTOMERIC SHIFT; X RAY CRYSTALLOGRAPHY;

EID: 3142742254     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.039     Document Type: Article

References (69)

1. Partly presented at the 10th Blue Danube Symposium on Heterocyclic Chemistry, Vienna, September 2003, poster PO78.
2. Elguero J., Marzin C., Linda P., Katritzky A.R. Advances in Heterocyclic Chemistry, Supplement 1: The Tautomerism of Heterocycles. 1976;Academic, New York. pp 313-336; and references cited therein
3. Minkin V.I., Garnovskii A.D., Elguero J., Katritzky A.R., Denisko O.V. The tautomerism of heterocycles: five-membered rings with two or more heteroatoms. Adv. Heterocycl. Chem. 76:2000;157-323
4. Elguero J. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives. Vol. 5:1984;Pergamon, Oxford. pp 167-303
5. Elguero J. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II: Pyrazoles. Vol. 3:1996;1-7 Pergamon, Oxford
6. Dorn H. J. Prakt. Chem. 315:1973;382-418. and references cited therein
7. Kleinpeter E., Koch A. J. Phys. Org. Chem. 14:2001;566-576
8. O'Connell M.J., Ramsay C.G., Steel P.J. Aust. J. Chem. 38:1985;401-409. and references cited therein
9. Uzoukwu A.B., Al-Juaid S.S., Hitchcock P.B., Smith J.D. Polyhedron. 12:1993;2719-2724
10. Akama Y., Shiro M., Ueda T., Kajitani; M. Acta Crystallogr. Sect. C. 51:1995;1310-1314. and references cited therein
11. Guard J.A.M., Steel P.J. Aust. J. Chem. 47:1994;1453-1459
12. Holzer W., Mereiter K., Plagens B. Heterocycles. 50:1999;799-818
13. Kurkovskaya L.N., Shapet'ko N.N., Vitvitskaya A.S., Kvitko A.Y. J. Org. Chem. USSR (Engl. Transl.). 13:1977;1618-1625
14. For some recent examples see: (a) Cingolani A., Effendy, Marchetti F., Pettinari C., Pettinari R., Skelton B.W., White A.H. Inorg. Chim. Acta. 329:2002;100-112
15. Marchetti F., Pettinari C., Pettinari R., Cingolani A., Leonesi D., Lorenzotti A. Polyhedron. 18:1999;3041-3050
16. Pettinari C., Marchetti F., Cingolani A., Bianchini G., Drozdov A., Vertlib V., Troyanov S. J. Organomet. Chem. 651:2002;5-14
17. Umetani S., Kawase Y., Le Q.T.H., Matsui M. J. Chem. Soc., Dalton Trans. 2000;2787-2791
18. Chiba P., Holzer W., Landau M., Bechmann G., Lorenz K., Plagens B., Hitzler M., Richter E., Ecker G. J. Med. Chem. 41:1998;4001-4011
19. Katritzky A.R., Karelson M., Harris P.A. Heterocycles. 32:1991;329-369
20. Heinisch G., Hollub C., Holzer W. J. Heterocycl. Chem. 28:1991;1047-1050
21. Holzer W., Schmid E. J. Heterocycl. Chem. 32:1995;1341-1349
22. Holzer W., Plagens B. Sci. Pharm. 64:1996;455-462. Chem. Abstr. 1996, 125, 300885
23. Holzer W., Plagens B., Lorenz K. Heterocycles. 45:1997;309-314
24. Holzer W., Hahn K., Brehmer T., Claramunt R.M., Pérez-Torralba M. Eur. J. Org. Chem. 2003;1209-1219
25. Holzer W., Claramunt R.M., Pérez-Torralba M., Guggi D., Brehmer T.H. J. Org. Chem. 68:2003;7943-7950
26. Holzer W., Krca I. Heterocycles. 60:2003;2323-2342
27. Claisen L., Haase E. Ber. Dtsch. Chem. Ges. 28:1895;35-41
28. Michaelis A. Liebigs Ann. Chem. 385:1911;1-102
29. Jensen B.S. Acta Chem. Scand. 13:1959;1668-1670
30. Patt S.L., Shoolery J.N. J. Magn. Reson. 46:1982;535-539
31. Neuhaus D., Williamson M.P. The Nuclear Overhauser Effect in Structural and Conformational Analysis. 1989;VCH, New York. pp 211-240
32. Davis D.G., Bax A. J. Am. Chem. Soc. 107:1985;7197-7198
33. Sarkar S.K., Bax A. J. Magn. Reson. 62:1985;109-112
34. Bax A., Subramanian S. J. Magn. Reson. 67:1986;565-569
35. Bax A. J. Magn. Reson. 57:1984;314-318
36. Jippo T., Kamo O., Nagayama K. J. Magn. Reson. 66:1986;344-348
37. Zeigan D., Kleinpeter E., Wilde H., Mann G. J. Prakt. Chem. 323:1981;188-198
38. Freyer W., Köppel H., Radeglia R., Malewski G. J. Prakt. Chem. 325:1983;238-250
39. Gil V.M.S., von Philipsborn W. Magn. Reson. Chem. 27:1989;409-430
40. 13C NMR-Spektroskopie. 1984;Thieme, Stuttgart. pp 461-475
41. Seel H., Günther H. J. Am. Chem. Soc. 102:1980;7051-7054
42. Takeuchi Y., Dennis N. Org. Magn. Reson. 7:1975;244-246
43. Begtrup M. J. Chem. Soc., Perkin Trans. 2. 1976;736-741
44. Begtrup M., Boyer G., Cabildo P., Cativiela C., Claramunt R.M., Elguero J., García J.I., Toiron C., Vedsø P. Magn. Reson. Chem. 31:1993;107-168
45. Holzer W., Jäger C., Slatin C. Heterocycles. 38:1994;2433-2448
46. Elguero J., Jimeno M.L., Yranzo G.I. Magn. Reson. Chem. 28:1990;807-811
47. Claramunt R.M., Sanz D., Boyer G., Catalán J., de Paz J.L.G., Elguero J. Magn. Reson. Chem. 31:1993;791-800
48. Bruix M., de Mendoza J., Claramunt R.M., Elguero J. Magn. Reson. Chem. 23:1985;367-374
49. Carmona D., Ferrer J., Oro L.A., Apreda M.C., Foces-Foces C., Cano F.H., Elguero J., Jimeno M.L. J. Chem. Soc., Dalton Trans. 1990;1463-1476
50. Begtrup M., Larsen P., Vedsø P. Acta Chem. Scand. 46:1992;972-980
51. Holzer W., Hahn K. J. Heterocycl. Chem. 40:2003;303-308
52. Holzer, W.; Laggner, C.; Singh, P. to be published.
53. Ernst L., Wray V., Chertkov V.A., Sergeyev N.M. J. Magn. Reson. 25:1977;123-139
54. Sándor P., Radics L. Org. Magn. Reson. 14:1980;98-102
55. Del Bene J.E., Elguero J., Alkorta I., Yáñez M., Mó O. J. Chem. Phys. 120:2004;3237-3243
56. Munakata, T.; Naka, Y.; Moriwaki M.; Goto, K. (Yoshitomi Pharma. Industries). Jap. Kokai Tokkyo Koho JP 55035066, 1980; Chem. Abstr. 1980, 93, 150250.
57. Maquestiau A., van Haverbeke Y., Vanovervelt J.C., Postiaux R. Bull. Soc. Chim. Belg. 85:1976;697-705
58. Palacios F., Ochoa de Retana A.M., Pagalday J. Tetrahedron. 55:1999;14451-14458
59. Schmidt F. Pharmazie. 11:1956;191-195
60. Bodendorf K., Popelak A. Liebigs Ann. Chem. 566:1950;84-89
61. Ito I. J. Pharm. Soc. Jpn. 76:1956;167-169. Chem. Abstr. 1956, 50, 74061
62. Ledrut J., Combes G., Swierkot H. Bull. Soc. Chim. Fr. 1950;232-238
63. Becke A.D. Phys. Rev. A. 38:1988;3098-3100
64. Becke A.D. J. Chem. Phys. 98:1993;5648-5652
65. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785-789
66. Ditchfield R., Hehre W.J., Pople J.A. J. Chem. Phys. 54:1971;724-728
67. Frisch M.J., Pople J.A., Krishnam R., Binkley J.S. J. Chem. Phys. 80:1984;3265-3269
68. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C., Pople, J. A. Gaussian 03; Gaussian, Inc.: Pittsburgh PA, 2003.
69. Barone V., Peralta J.E., Contreras R.H., Snyder J.P. J. Phys. Chem. A. 106:2002;5607-5612