Unexpected formation of β-lactams and penem isosteres from mesoionics: Sequential ring-opening-rearrangement of [3 + 2] cycloadducts

Chemical Communications

Volumn , Issue 16, 1999, Pages 1589-1590

  Avalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Hursthouse, Michael B ^b   Jiménez, José L ^a   Light, Mark E ^b   López, Ignacio ^a   Palacios, Juan C ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMPHOLYTE; BETA LACTAM; HETEROCYCLIC COMPOUND; PENEM DERIVATIVE; THIOISOMUNCHNONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS;

EID: 0033592142     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904333k     Document Type: Article

References (17)

1. W. D. Ollis and C. A. Ramsden, Adv. Heterocycl. Chem., 1976, 19, 1; C. G. Newton and C. A. Ramsden, Tetrahedron, 1982, 38, 2965; W. D. Ollis, S. P. Stanforth and C. A. Ramsden, Tetrahedron, 1985, 41, 2239.
2. W. D. Ollis and C. A. Ramsden, Adv. Heterocycl. Chem., 1976, 19, 1; C. G. Newton and C. A. Ramsden, Tetrahedron, 1982, 38, 2965; W. D. Ollis, S. P. Stanforth and C. A. Ramsden, Tetrahedron, 1985, 41, 2239.
3. W. D. Ollis and C. A. Ramsden, Adv. Heterocycl. Chem., 1976, 19, 1; C. G. Newton and C. A. Ramsden, Tetrahedron, 1982, 38, 2965; W. D. Ollis, S. P. Stanforth and C. A. Ramsden, Tetrahedron, 1985, 41, 2239.
4. K. T. Potts, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 2, ed. A. Padwa, Wiley, New York, 1984, pp. 1-82; M. H. Osterhout, W. R. Nadler and A. Padwa, Synthesis, 1994, 123.
5. K. T. Potts, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 2, ed. A. Padwa, Wiley, New York, 1984, pp. 1-82; M. H. Osterhout, W. R. Nadler and A. Padwa, Synthesis, 1994, 123.
6. P. Areces, M. Avalos, R. Babiano, L. González, J. L. Jiménez, J. C. Palacios and M. D. Pilo, Carbohydr. Res., 1991, 222, 99; M. Avalos, R. Babiano, M. J. Diánez, J. Espinosa, M. D. Estrada, J. L. Jiménez, A. López-Castro, M. M. Méndez and J. C. Palacios, Tetrahedron, 1992, 48, 4193; C. O. Kappe, K. Peters and E.-M. Peters, J. Org. Chem., 1997, 62, 3109.
7. P. Areces, M. Avalos, R. Babiano, L. González, J. L. Jiménez, J. C. Palacios and M. D. Pilo, Carbohydr. Res., 1991, 222, 99; M. Avalos, R. Babiano, M. J. Diánez, J. Espinosa, M. D. Estrada, J. L. Jiménez, A. López-Castro, M. M. Méndez and J. C. Palacios, Tetrahedron, 1992, 48, 4193; C. O. Kappe, K. Peters and E.-M. Peters, J. Org. Chem., 1997, 62, 3109.
8. P. Areces, M. Avalos, R. Babiano, L. González, J. L. Jiménez, J. C. Palacios and M. D. Pilo, Carbohydr. Res., 1991, 222, 99; M. Avalos, R. Babiano, M. J. Diánez, J. Espinosa, M. D. Estrada, J. L. Jiménez, A. López-Castro, M. M. Méndez and J. C. Palacios, Tetrahedron, 1992, 48, 4193; C. O. Kappe, K. Peters and E.-M. Peters, J. Org. Chem., 1997, 62, 3109.
9. M. Avalos, R. Babiano, A. Cabanillas, P. Cintas, M. J. Diánez, M. D. Estrada, J. L. Jiménez, A. López-Castro, J. C. Palacios and S. P. Garrido, J. Chem. Soc., Chem. Commun., 1995, 2213;
10. M. Avalos, R. Babiano, A. Cabanillas, P. Cintas, F. J. Higes, J. L. Jiménez and J. C. Palacios, J. Org. Chem., 1996, 61, 3738.
11. P. Areces, M. Avalos, R. Babiano, L. González, J. L. Jiménez, M. M. Méndez and J. C. Palacios, Tetrahedron Lett., 1993, 34, 2999.
12. The Chemistry β-Lactams, ed. M. I. Page, Blackie, London, 1992; The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993.
13. The Chemistry β-Lactams, ed. M. I. Page, Blackie, London, 1992; The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993.
14. P. D. Edwards and P. R. Bernstein, Med. Res. Rev., 1994, 14, 127; O. A. Mascaretti, C. E. Boschetti, G. O. Danelon, E. G. Mata and O. A. Roveri, Curr. Med. Chem., 1995, 1, 441.
15. P. D. Edwards and P. R. Bernstein, Med. Res. Rev., 1994, 14, 127; O. A. Mascaretti, C. E. Boschetti, G. O. Danelon, E. G. Mata and O. A. Roveri, Curr. Med. Chem., 1995, 1, 441.
16. R. J. Simonds, Chemistry of Biomolecules - An Introduction, The Royal Society of Chemistry, Cambridge, 1992, pp. 216-258.
17. E. Funke and R. Huisgen, Chem. Ber., 1971, 104, 3222.