Spiro-fused (C2)-azirino-(C4)-pyrazolones, a new heterocyclic system. Synthesis, spectroscopic studies and X-ray structure analysis

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 7943-7950

  Holzer, Wolfgang ^a   Claramunt, Rosa M ^b   Pérez Torralba, Marta ^b   Guggi, Davide ^a   Brehmer, Thomas H ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ETHERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; X RAY ANALYSIS;

HETEROCYCLIC SYSTEM;

KETONES;

1 BENZYL 7 METHYL 2 PHENYL 1,5,6 TRIAZASPIRO[2.4]HEPTA 1,6 DIEN 4 ONE; 2 BENZYL 2,4 DIHYDRO 4 [(HYDROXYAMINO)PHENYLMETHYLENE] 5 METHYL 3H PYRAZOL 3 ONE; 2 BENZYL 2,4 DIHYDRO 4 [1 (HYDROXYAMINO)ETHYLIDENE] 5 METHYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 2,5 DIMETHYL 4 [(HYDROXYAMINO)(2 THIENYL)METHYLENE] 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 2,5 DIMETHYL 4 [(HYDROXYAMINO)(PHENYL)METHYLENE] 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 2,5 DIMETHYL 4 [(HYDROXYAMINO)PHENYLMETHYLENE] 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(HYDROXYAMINO)METHYLENE] 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(HYDROXYAMINO)METHYLIDENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [(HYDROXYAMINO)PHENYLMETHYLENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,4 DIHYDRO 4 [1 (HYDROXYAMINO)ETHYLIDENE] 5 METHYL 2 PHENYL 3H PYRAZOL 3 ONE; 2,5 DIPHENYL 7 METHYL 1,5,6 TRIAZASPIRO[2.4]HEPTA 1,6 DIEN 4 ONE; 4 ACYL 5 HYDROXY 3 METHYL 1H PYRAZOLE; 7 METHYL 1,5,6 TRIAZASPIRO[2.4]HEPTA 1,6 DIEN 4 ONE; AZIRINE DERIVATIVE; ETHER; FUSED HETEROCYCLIC RINGS; HYDROXYLAMINE; ISOCYANIC ACID DERIVATIVE; OXIME DERIVATIVE; POTASSIUM CARBONATE; PYRAZOLONE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0142026605     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030131t     Document Type: Article

References (63)

1. Presented in part at the 8th Blue Danube Symposium on Heterocyclic Chemistry, Bled (Slovenia), September 2000, poster no. 30.
2. For recent examples see, e.g.: (a) Pettinari, C.; Marchetti, F.; Cingolani, A.; Bianchini, G.; Drozdov, A.; Vertlib, V.; Troyanov, S. J. Organomet. Chem. 2002, 651, 5-14.
3. (b) Cingolani, A.; Effendy, Marchetti, F.; Pettinari, C.; Pettinari, R.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2002, 329, 100-112.
4. (c) Pettinari, C.; Marchetti, F.; Pettinari, R.; Drozdov, A.; Troyanov, S.; Voloshin, A. I.; Shavaleev, N. M. J. Chem. Soc., Dalton Trans. 2002, 1409-1415.
5. (d) Umetani, S.; Kawase, Y.; Le, Q. T. H.; Matsui, M. J. Chem. Soc., Dalton Trans. 2000, 2787-2791.
6. (e) Pettinari, C.; Rafaiani, G.; Lobbia, G. G.; Lorenzotti, A.; Bonati, F.; Bovio, B. J. Organomet. Chem. 1991, 405, 75-92.
7. (f) López, R.; León, G.; Oliva, A. J. Heterocyl. Chem. 1995, 32, 1377-1379.
8. Chiba, P.; Holzer, W.; Landau, M.; Bechmann, G.; Lorenz, K.; Plagens, B. ; Hitzler, M.; Richter, E.; Ecker, G. J. Med. Chem. 1998, 41, 4001-4011.
9. (a) Kirschke, K. 1H-Pyrazole. In Houben-Weyl: Methoden der Organischen Chemie; Thieme: Stuttgart, New York, 1994; Vol. E8b, pp 399-763.
10. (b) Stanovnik, B.; Svete, J. Pyrazoles. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thieme: Stuttgart-New York, 2002; Vol. 12, pp 15-225.
11. (a) Gelin, S.; Chantegrel, B.; Nadi, A. I. J. Org. Chem. 1983, 48, 4078-4082.
12. (b) Chantegrel, B.; Nadi, A. I.; Gelin, S. Synthesis 1983, 844-845.
13. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The Tautomerism of Heterocycles. In Advances in Heterocyclic Chemistry, Suppl. 1; Academic Press: New York, 1976; pp 313-336 and references therein.
14. Elguero, J. In Comprehensive Heterocyclic Chemistry: Pyrazoles and Their Benzo Derivatives; Katritzky, A. R., Rees, C. W., Eds., Pergamon Press: Oxford, 1984; Vol. 5, pp 167-303.
15. Elguero, J. In Comprehensive Heterocyclic Chemistry II: Pyrazoles; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 3, pp 1-75.
16. Kurkovskaya, L. N.; Shapet'ko, N. N.; Vitvitskaya, A. S.; Kvitko, A. Y. J. Org. Chem. USSR (Engl. Transl.) 1977, 13, 1618-1625.
17. O'Connell, M. J.; Ramsay, C. G.; Steel, P. J. Aust. J. Chem. 1985, 38, 401-409 and references therein.
18. Akama, Y.; Shiro, M.; Ueda, T.; Kajitani, M. Acta Crystallogr. 1995, C51, 1310-1314 and references therein.
19. Holzer, W.; Mereiter, K.; Plagens, B. Heterocycles 1999, 50, 799-818.
20. Heinisch, G.; Hollub, C.; Holzer, W. J. Heterocycl. Chem. 1991, 28, 1047-1050.
21. Holzer, W.; Schmid, E. J. Heterocycl. Chem. 1995, 32, 1341-1349.
22. Holzer, W.; Plagens, B. Sci. Pharm. 1996, 64, 455-462.
23. Holzer, W.; Plagens, B.; Lorenz, K. Heterocycles 1997, 45, 309-314.
24. Holzer, W.; Hahn, K.; Brehmer, T.; Claramunt, R. M.; Pé rez-Torralba, M. Eur. J. Org. Chem. 2003, 1209-1219.
25. Stokker, G. J. Org. Chem. 1983, 48, 2613-2615
26. Pawar, R. A.; Patil, A. A. Indian J. Chem. Sect. B 1994, 33, 156-158.
27. Jensen, B. S. Acta Chem. Scand. 1959, 13, 1668-1670.
28. Katritzky, A. R.; Karelson, M.; Harris, P. A. Heterocycles 1999, 32, 329-369.
29. Hawkes, G. E.; Herwig, K.; Roberts, J. D. J. Org. Chem. 1974, 39, 1017-1028.
30. Freyer, W.; Tomaschewski, G. J. Prakt. Chem. 1977, 319, 895-904.
31. Otto, H.-H.; Schmelz, H. Monatsh. Chem. 1980, 111, 53-61.
32. Kölle, U.; Kolb, B.; Mannschreck, A. Chem. Ber. 1980, 113, 2545-2565.
33. Hennig, L.; Mann, G. Z. Chem. 1988, 28, 364-365.
34. Tagawa, Y.; Goto, Y. Heterocycles 1987, 26, 2921-2939.
35. Bauer, L.;Exner, O. Angew. Chem. 1974, 86, 419-428; Angew. Chem., Int. Ed. Engl. 1974, 13, 376-384.
36. Bauer, L.;Exner, O. Angew. Chem. 1974, 86, 419-428; Angew. Chem., Int. Ed. Engl. 1974, 13, 376-384.
37. Padwa, A.; Woolhouse, A. D. Aziridines, Azirines and Fused-Ring Derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 47-93.
38. Pearson, W. H.; Lian, B. W. Aziridines and Azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 1A, pp 1-60.
39. Pinho e Melo, T. M. V. D.; Lopes, C. S. J.; Rocha Gonsalves, A. M. d'A.; Storr, R. C. Synthesis 2002, 605-608.
40. (a) Padwa, A.; Woolhouse, A. D. Aziridines, Azirines and Fused-Ring Derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 82-83.
41. (b) Padwa, A.; Woolhouse, A. D. Aziridines, Azirines and Fused-Ring Derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 52-54.
42. Smalley, R. K. 1,2-Benzoxazole. In Houben-Weyl: Methoden der Organischen Chemie; Thieme: Stuttgart, New York, 1993; Vol. E8a, pp 226-348.
43. Poissonnet, G. Synth. Commun. 1997, 27, 3839-3846.
44. Holzer, W.; Hahn, K. J. Heterocycl. Chem. 2003, 40, 303-308.
45. Davis, D. G.; Bax, A. J. Am. Chem. Soc. 1985, 107, 7197-7198.
46. Bax, A. J. Magn. Reson. 1984, 57, 314-318.
47. Jippo, T.; Kamo, O.; Nagayama, K. J. Magn. Reson. 1986, 66, 344-348.
48. Sarenko, A. S.; Kvitko, I. Y.; Efros, L. S. Khim. Geterotsikl. Soedin. 1972, 799-804; Chem. Heterocycl. Compd. (N.Y.) 1972, 722-727.
49. Sarenko, A. S.; Kvitko, I. Y.; Efros, L. S. Khim. Geterotsikl. Soedin. 1972, 799-804; Chem. Heterocycl. Compd. (N.Y.) 1972, 722-727.
50. Wise, L. D.; Butler, D. E.; DeWald, H. A.; Lustgarten, D. M.; Pattison, I. C.; Schweiss, D. N.; Coughenour, L. L.; Downs, D. A.; Heffner, T. G.; Pugsley, T. A. J. Med. Chem. 1987, 30, 1807-1812.
51. Maquestiau, A.; Van Haverbeke, Y.; Vanovervelt, J. C.; Postiaux, R. Bull. Soc. Chim. Belg, 1976, 85, 697-705.
52. Kira, M. A.; Bruckner-Wilhelms, A. Hung. Acta Chim. 1968, 56, 47-51.
53. Li, C.; Hou, J.-G. Talanta 1997, 44, 729-732.
54. Curtius, T. J. Prakt. Chem. 1912, 85, 37-52.
55. Rana, A. K.; Shah, J. R. Indian J. Chem. Sect. A 1981, 20A, 142-144.
56. (a) Ridi, M.; Checci, S. Ann. Chim. 1953, 43, 816.
57. (b) Becher, J.; Jørgenson, P. L.; Pluta, K.; Krake, N. J.; Fält-Hansen, B. J. Org. Chem. 1992, 57, 2127-2134.
58. SIR92: Program for Crystal Structure Solution. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343-350.
59. SHELX97: Programs for Crystal Structure Analysis (Release 97-2). Sheldrick, G. M. Institut für Anorganische Chemie der Universität: Tammanstrasse 4, D-37077 Göttingen, Germany, 1998.
60. PLATON: (a) Van der Sluis, P.; Spek, A. L. Acta Cryst., Sect. A 1990, A46, 194-201.
61. (b) Spek, A. L. PLATON: A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 1988.
62. DIAMOND 2.1a: Visual Crystal Structure Information System; Brandenburg, K. Universität Bonn: Bonn, Germany, 1999.
63. WINGX v1.63.01: System of Windows Programs for the Solution, Refinement and Analysis of Single-Crystal X-ray Diffraction Data. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.