1,3-Dipolar cycloadditions of (4R*,5R*)-1-alkylidene-4- (benzoylamino)-5-phenyl-3-pyrazolidinon-1-azomethine imines

Journal of Heterocyclic Chemistry

Volumn 45, Issue 1, 2008, Pages 181-188

  Pezdirc, Lidija ^a   Grošelj, Uroš ^a   Meden, Anton ^a   Stanovnik, Branko ^a   Svete, Jurij ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

3 PYRAZOLIDINONE; ACETONE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKENE DERIVATIVE; ALKYL GROUP; AZO COMPOUND; AZOMETHINE DERIVATIVE; BUTYRALDEHYDE; IMINE; PHENYL GROUP; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 38949148294     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450121     Document Type: Article

References (50)

1. (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A. Ed, John Wiley & Sons, New York, Vol 1, 1984.
2. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A. Ed, John Wiley & Sons, New York, Vol 2, 1984.
3. (c) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H. Eds, John Wiley & Sons, Hoboken, New Jersey, 2003.
4. Gothelf, V. K.; Jørgensen, K. A. In Asymmetric Reactions in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, Padwa, A.; Pearson, W. H. Eds, John Wiley & Sons, Hoboken, New Jersey, 2003, pp 817-899.
5. Grashey, R. In Azomethine Imines in 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed, John Wiley & Sons, New York, 1984, Vol 1, pp 733-814.
6. Schantl, J. G. In Azomethine Imines in Science of Synthesis, Houben-Weyl Methods of Organic Transformations; Georg Thieme Verlag, Stuttgart, 2004, Vol. 27, pp 731-824.
7. Stanovnik, B. Tetrahedron 1991, 47, 2925.
8. Žličar, M.; Stanovnik, B.; Tišler, M. Tetrahedron 1992, 48, 7965.
9. Žličar, M.; Stanovnik, B.; Tišler, M. J. Heterocycl. Chem. 1993, 30, 1209.
10. Stanovnik, B.; Jelen, B.; Žličar, M. Il Farmaco 1993, 48, 231.
11. Stanovnik, B.; Jelen, B.; Turk, C.; Žličar, M.; Svete, J. J. Heterocycl. Chem. 1998, 35, 1187.
12. Dorn, H. Chem. Heterocycl. Compd. USSR 1981, 3; and references cited therein.
13. Claramunt, R. M.; Elguero, J. Org. Proc. Prep. Int. 1991, 23, 273; and references cited therein.
14. Ternansky, R. J.; Draheim, S. E. Tetrahedron 1992, 48, 777.
15. Svete, J.; Prešeren, A.; Stanovnik, B.; Golič, L.; Golič Grdadolnik, S. J. Heterocycl. Chem. 1997, 34, 1323.
16. Prešeren, A.; Svete, J.; Stanovnik, B. J. Heterocycl. Chem. 1999, 36, 799.
17. Zupančič, S.; Svete, J.; Stanovnik, B. J. Heterocycl. Chem. 1999, 36, 607.
18. Chuang, T.-H.; Sharpless, K. B. Helv. Chim. Acta 2000, 83, 1734.
19. Panfil, I.; Urbanczyk-Lipkowska, Z.; Suwinska, K.; Solecka, J.; Chmielewski, M. Tetrahedron 2002, 58, 1199.
20. Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 10778.
21. Suarez, A.; Downey, C. W.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11244.
22. Pezdirc, L.; Jovanovski, V.; Bevk, D.; Jakše, R.; Pirc, S.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron 2005, 61, 3977.
23. Pezdirc, L.; Cerkovnik, J.; Pirc, S.; Stanovnik, B.; Svete, J. Tetrahedron 2007, 63, 991.
24. (a) Pezdirc, L.; Bevk, D.; Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. J. Comb. Chem. 2007, 9, 717.
25. (b) Pezdirc, L.; Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron Lett. 2007, 48, 5205.
26. Roussi, F.; Bonin, M.; Chiaroni, A.; Micouin, L.; Riche, C.; Husson, H.-P. Tetrahedron Lett. 1999, 40, 3727.
27. Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170.
28. Chauveau, A.; Martens, T.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2002, 1885.
29. Chung, F.; Chauveau, A.; Seltki, M.; Bonin, M.; Micouin, L. Tetrahedron Lett. 2004, 45, 3127.
30. (a) Chen, J.-H.; Venkatesham, U.; Lee, L.-C.; Chen, K. Tetrahedron 2006, 62, 887.
31. (b) Cusan, C.; Spalluto, G.; Prato, M.; Adams, M.; Bodensieck, A.; Bauer, R.; Tubaro, A.; Bernardi, P.; Da Ros, T. Il Farmaco 2005, 60, 327.
32. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron, 1997, 53, 12789.
33. (a) Dotn, H.; Otto, A. Chem. Ber. 1968, 101, 3287.
34. (b) Dorn, H.; Ozegowski, R.; Gründemann, E. J. prakt. Chem. 1979, 321, 565.
35. (c) Dorn, H. Tetrahedron Lett. 1985, 26, 5123.
36. (a) Oppolzer, W. Tetrahedron Lett. 1970, 11, 2199.
37. (b) Oppolzer, W. Tetrahedron Lett. 1972, 13, 1707.
38. For a review see: (a) Stanovnik, B.; Svete, J. Targets in Heterocyclic Systems 2000, 4, 105.
39. (b) Svete, J. J. Heterocycl. Chem. 2002, 39, 437.
40. (c) Svete, J. ARKIVOC 2006, Part vii, 35.
41. (a) Turk, C.; Svete, J.; Stanovnik, B.; Golič, L.; Golobič, A.; Selič, L. Org. Lett. 2000, 2, 423.
42. (b) Turk, C.; Svete, J.; Stanovnik, B.; Golič, L.; Golič Grdadolnik, S.; Golobič, A.; Selič, L. Helv. Chim. Acta 2001, 84, 146.
43. (c) Turk, C.; Golič, L.; Selič, L.; Svete, J.; Stanovnik, B. ARKIVOC 2001, Part v, 87.
44. (a) Huisgen, R. In 1,3-Dipolar Cycloadditions-Introduction, Survey, Mechanism in 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed, John Wiley & Sons, New York, 1984, Vol 1, pp 1-176.
45. (b) Houk, K. N.; Yamaguchi, K. In Theory of 1,3-Dipolar Cycloadditions in 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed, Vol 2, John Wiley & Sons, New York, 1984, pp 407-450.
46. Collect Software. Nonius, BV, Delft,The Netherlands, 1998.
47. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
48. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115.
49. Hall, S. R.; King, G. S. D.; Stewart, J. M. The Xtal3.4 User's Manual; University of Western Australia: Lamb, Perth, 1995.
50. Wang, H.; Robertson, B. E. Structure and Statistics in Crystallography; Wilson, A. J. C., Ed, Adenine Press, New York, 1985.