Competitive formation of β-enaminones and 3-amino-2(5H)-furanones from the isoxazolidine system: A combined synthetic and quantum chemical study

European Journal of Organic Chemistry

Volumn , Issue 30, 2010, Pages 5897-5905

  Iannazzo, Daniela ^a   Brunaccini, Elisa ^a   Giofrè, Salvatore V ^a   Piperno, Anna ^a   Romeo, Giovanni ^a   Ronsisvalle, Simone ^b   Chiacchio, Maria A ^b   Lanza, Giuseppe ^b   Chiacchio, Ugo ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Enaminones; 1,3 Dipolar cycloaddition; 2(5H) Furanones; Density function calculations; Isoxazolidines

Indexed keywords

EID: 78249289674     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000579     Document Type: Article

References (46)

1. C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845 - 1854.
2. C.-H. Tan, A. B. Holmes, Chem. Eur. J. 2001, 7, 1845 - 1854.
3. U. Chiacchio, A. Padwa, G. Romeo, Curr. Org. Chem. 2009, 13, 422 - 447.
4. S. M. Lait, D. A. Rankic, B. A. Keay, Chem. Rev. 2007, 107, 767 - 796.
5. G. Singh, M. P. S. Ishar, V. Gupta, M. Kalyan, S. S. Bhella, Tetrahedron 2007, 73, 4773 - 4778.
6. G. Pandey, P. Banerjee, R. Gadre, Chem. Rev. 2006, 106, 4484 - 4517.
7. U. Chiacchio, A. Rescifina, M. G. Saita, D. Iannazzo, G. Romeo, J. A. Mates, T. Tejero, P. Merino, J. Org. Chem. 2005, 70, 899 - 9001.
8. P. Merino, in: Science of Synthesis, Houben-Weyl Methods of Molecular Transformations (Ed.:, A. Padwa), Thieme, Stuttgart, 2004, pp. 511-580.
9. A. R. Minter, B. B. Brennan, A. K. Mapp, J. Am. Chem. Soc. 2004, 126, 10504 - 10505.
10. A. Padwa, W. H. Pearson, in: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry towards Heterocycles and Natural Products, John Wiley & Sons, Hoboken, N. J., 2003, vol. 2, pp. 539-621.
11. Tejero, U. Chiacchio, G. Romeo, D. Iannazzo, R. Romeo, P. Merino, J. A. Mates, J. Revuelta, Tetrahedron: Asymmetry 2002, 13, 173 - 190.
12. U. Chiacchio, A. Corsaro, V. Pistarà, A. Rescifina, D. Iannazzo, A. Piperno, G. Romeo, R. Romeo, G. Grassi, Eur. J. Org. Chem. 2002, 1206 - 1212.
13. U. Chiacchio, A. Corsaro, A. Rescifina, M. Bkaithan, A. Piperno, T. Privitera, G. Romeo, Tetrahedron 2001, 57, 3425 - 3433.
14. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, A. Rescifina, R. Romeo, G. Romeo, Tetrahedron Lett. 2001, 42, 1777 - 1780.
15. U. Chiacchio, A. Rescifina, G. Romeo, in: Targets in Heterocyclic Systems. Chemistry and Properties (Eds.:, O. Attanasi, D. Spinelli,), Italian Society of Chemistry, 1997, vol. 1, pp. 225-276.
16. T. B. Nguyen, A. Beauseigneur, A. Martel, R. Dhal, M. Laurent, G. Dujardin, J. Org. Chem. 2010, 75, 611 - 620.
17. A. Bdoiu, Y. Brinkmann, F. Viton, E. P. Künding, Pure App. Chem. 2008, 80, 1013 - 1018.
18. T. B. Nguyen, A. Martel, R. Dhal, G. Dujardin, J. Org. Chem. 2008, 73, 2621 - 2632.
19. R. Romeo, D. Iannazzo, A. Piperno, M. A. Chiacchio, Eur. J. Org. Chem. 2005, 2368 - 2373.
20. G. Romeo, D. Iannazzo, A. Piperno, R. Romeo, A. Corsaro, A. Rescifina, U. Chiacchio, Mini-Rev. Org. Chem. 2005, 2, 59 - 77.
21. P. Merino, Compt. Rend. Chim. 2005, 8, 775 - 788.
22. U. Chiacchio, A. Piperno, A. Rescifina, G. Romeo, N. Uccella, Tetrahedron 1998, 54, 5695 - 5708.
23. F. Casuscelli, M. R. Di Bella, R. Ficarra, S. Melardi, G. Romeo, U. Chiacchio, A. Rescifina, Gazz. Chim. It. 1997, 127, 367 - 371.
24. U. Chiacchio, A. Liguori, G. Romeo, G. Sindona, N. Uccella, Heterocycles 1993, 36, 799 - 817.
25. S. Cicchi, A. Goti, A. Brandi, A. Guarna, F. De Sarlo, Tetrahedron Lett. 1990, 31, 3351 - 3354.
26. J. W. Grate, G. C. Frye, in: Sensors Update (Eds.:, H. Baltes, W. Göpel, J. Hesse), Wiley-VCH, Weinheim, 1996, vol. 2, pp. 10-20.
27. J. Ariza, J. Font, R. M. Ortuno, Tetrahedron Lett. 1991, 32, 1979 - 1982.
28. U. Chiacchio, D. Iannazzo, A. Piperno, V. Pistarà, A. Rescifina, G. Romeo, R. Romeo, Tetrahedron 2004, 60, 6593 - 6596.
29. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, A. Procopio, A. Rescifina, G. Romeo, R. Romeo, J. Org. Chem. 2002, 67, 4380 - 4383.
30. F. Casuscelli, U. Chiacchio, M. R. Di Bella, A. Rescifina, G. Romeo, R. Romeo, N. Uccella, Tetrahedron 1995, 51, 8605 - 8612.
31. D. Iannazzo, A. Piperno, G. Romeo, R. Romeo, U. Chiacchio, A. Rescifina, E. Balestrieri, B. Macchi, A. Mastino, R. Cortese, Bioorg. Med. Chem. 2008, 16, 9610 - 9615.
32. T. Persson, J. Nielsen, Org. Lett. 2006, 8, 3219 - 3222.
33. Y. O. Ko, Y. S. Chun, C.-L. Park, Y. Kim, H. Shin, S. Ahn, J. H.-S. Lee, Org. Biomol. Chem. 2009, 7, 1132 - 1136.
34. T. Hashimoto, M. Omote, K. Maruoka, Org. Biomol. Chem. 2008, 6, 2263 - 2265.
35. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, G. Romeo, R. Romeo, M. G. Saita, A. Rescifina, Eur. J. Org. Chem. 2007, 4758 - 4764.
36. P. Merino, T. Tejero, U. Chiacchio, G. Romeo, A. Rescifina, Tetrahedron 2007, 63, 1448 - 1458.
37. K. R. R. Kumar, H. Mallesha, K. S. Rangappa, Synth. Commun. 2003, 33, 1545 - 1555.
38. P. Merino, S. Franco, F. L. Merchan, T. Tejero, J. Org. Chem. 2000, 65, 5575 - 5589.
39. S. Kanemasa, N. Ueno, M. Shirahase, Tetrahedron Lett. 2002, 43, 657 - 660.
40. To better analyze these aspects, additional calculations have been performed by using an alternative BPW91-DFT parametrization and traditional ab initio MP2 methods with the 6-31+G(d,p) basis set and including solvent effects. The great tendency toward aldehyde elimination from "free" isoxazolidine derivatives is confirmed and, for example, 13-II at the MP2 level formaldehyde expulsion releases more than 20 kcal/mol. Nevertheless, the thermodynamic drive for ring degradation is less pronounced when the traditional MP2 is used with respect to DFT-based methods.
41. C.-Y. Liu, X. Wang, T. Furuyama, S. Yasuike, A. Muranaka, K. Morokuma, M. Uchiyama, Chem. Eur. J. 2010, 16, 1780 - 1784.
42. G. Lanza, I. L. Fragalà, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 8257 - 8258.
43. G. Lanza, I. L. Fragalà, T. J. Marks, J. Am. Chem. Soc. 2000, 122, 12764 - 12777.
44. G. Lanza, I. L. Fragalà, T. J. Marks, Organometallics 2002, 21, 5594 - 5612.
45. Gaussian 09, Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. R. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C, Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
46. J. Hara, Y. Inouye, H. Kakisawa, Bull. Chem. Soc. Jpn. 1981, 54, 3871 - 3872.