Microwave-Assisted [3 + 2] Cycloadditions of Azomethine Ylides

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4915-4918

  Bashiardes, George ^a   Safir, Imad ^a   Mohamed, Achmet Said ^a   Barbot, Francis ^a   Laduranty, Joelle ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AZOMETHINE YLIDE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; SOLVENT;

ARTICLE; CYCLOADDITION; DRUG PURITY; DRUG SYNTHESIS; METHODOLOGY; MICROWAVE RADIATION; REACTION TIME;

EID: 0347683357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0361195     Document Type: Article

References (19)

1. Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223 and references therein.
2. Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851-10870. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223 and references therein.
3. Examples: Alexandre, F.-R.; Berecibar, A.; Wrigglesworth, R.; Besson, T. Tetrahedron Lett. 2003, 44, 4455-4458. Jiao, G.-S.; Castro, J. C.; Thorensen, L. H.; Burgess, K. Org. Lett. 2003, 5, 3675-3677. Paul, S.; Gupta, M.; Gupta, R.; Loupy, A. Synthesis 2002, 75.
4. Examples: Alexandre, F.-R.; Berecibar, A.; Wrigglesworth, R.; Besson, T. Tetrahedron Lett. 2003, 44, 4455-4458. Jiao, G.-S.; Castro, J. C.; Thorensen, L. H.; Burgess, K. Org. Lett. 2003, 5, 3675-3677. Paul, S.; Gupta, M.; Gupta, R.; Loupy, A. Synthesis 2002, 75.
5. Examples: Alexandre, F.-R.; Berecibar, A.; Wrigglesworth, R.; Besson, T. Tetrahedron Lett. 2003, 44, 4455-4458. Jiao, G.-S.; Castro, J. C.; Thorensen, L. H.; Burgess, K. Org. Lett. 2003, 5, 3675-3677. Paul, S.; Gupta, M.; Gupta, R.; Loupy, A. Synthesis 2002, 75.
6. De La Hoz, A.; Diaz-Ortiz A.; Langa, F. In Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Germany, 2003. Cheng, Q.; Zhang, W.; Tagami, Y.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 2001, 452-456.
7. De La Hoz, A.; Diaz-Ortiz A.; Langa, F. In Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Germany, 2003. Cheng, Q.; Zhang, W.; Tagami, Y.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 2001, 452-456.
8. Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2003, 44, 8417-8420.
9. Pinna, G. A.; Pirisi, M. A.; Chelucci, G.; Mussinu, J. M.; Murineddu, G. ; Loriga, G.; D'Aquila, P. S.; Serra, G. Bioorg. Med. Chem. 2002, 10, 2485-2496. Bolognesi, M. L.; Andrisano, V.; Bartolini, M.; Minarini, A.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 2001, 44, 105-109. Escolano, C.; Jones, K. Tetrahedron Lett. 2000, 41, 8951-8955.
10. Pinna, G. A.; Pirisi, M. A.; Chelucci, G.; Mussinu, J. M.; Murineddu, G. ; Loriga, G.; D'Aquila, P. S.; Serra, G. Bioorg. Med. Chem. 2002, 10, 2485-2496. Bolognesi, M. L.; Andrisano, V.; Bartolini, M.; Minarini, A.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 2001, 44, 105-109. Escolano, C.; Jones, K. Tetrahedron Lett. 2000, 41, 8951-8955.
11. Pinna, G. A.; Pirisi, M. A.; Chelucci, G.; Mussinu, J. M.; Murineddu, G. ; Loriga, G.; D'Aquila, P. S.; Serra, G. Bioorg. Med. Chem. 2002, 10, 2485-2496. Bolognesi, M. L.; Andrisano, V.; Bartolini, M.; Minarini, A.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 2001, 44, 105-109. Escolano, C.; Jones, K. Tetrahedron Lett. 2000, 41, 8951-8955.
12. Broggini, G.; Zecchi, G. Synthesis 1996, 1280-1282.
13. Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175-7178. Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960-1968. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537-540.
14. Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175-7178. Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960-1968. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537-540.
15. Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175-7178. Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960-1968. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537-540.
16. Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175-7178. Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960-1968. Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213-2230. Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537-540.
17. Reactions were carried out under atmospheric pressure on a CEM Discover apparatus.
18. Vo Quang, L.; Gaessler, H.; Vo Quang, Y. Ang. Chem., Int. Ed. Engl. 1981, 20, 880-881.
19. Rhee, M-H.; Vogel, Z.; Barg, J.; Bayewitch, M.; Levy, R.; Hanuš, L.; Breuer, A.; Mechoulam, R. J. Med. Chem. 1997, 40, 3228-3233.