New intramolecular cyclization and rearrangement processes based on the radical aryl-aryl coupling of arylsubstituted 2-azetidinones

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6589-6592

  Alcaide, Benito ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE; BETA LACTAM; POLYCYCLIC AROMATIC COMPOUND; RADICAL; TIN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032171497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01373-2     Document Type: Article

References (31)

1. 1. Some examples: (a) Ishiguro, M.; Imajo, S. J. Med. Chem. 1996, 39, 2207.
2. (b) Deraniyagala, S. A.; Adediran, S. A.; Pratt, R. F. J. Org. Chem. 1995, 60, 1619.
3. (c) Page, M. I.; Webster, P.; Ghosez, L. J. Chem. Soc., Perkin Trans. 2 1990, 805.
4. For a recent paper on the experimental determination of strain in 2-azetidinone nucleus, see: (d) Roux, M. V.; Jiménez, P.; Dávalos, J. Z.; Castaño, O.; Molina, M. T.; Notario, R.; Herreros, M.; Abboud, J.-L. M. J. Am. Chem. Soc. 1996, 118, 12735.
5. 2. The Organic Chemistry of β-Lactams, Georg, G. I. Ed.; VCH Publishers: New York, 1993.
6. 3. The following recent examples are illustrative: (a) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Sierra, M. A.; Monge, A. J. Org. Chem. 1996, 61, 9156.
7. (b) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819.
8. (c) Kita, Y.; Shibata, N.; Kawano, N.; Yoshida, N.; Matsumoto, K.; Takebe, Y. J Chem. Soc., Perkin Trans.I 1996, 2321.
9. (d) Alcaide, B.; Pérez-Castells, J.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1995, 60, 6012.
10. A review dealing with the special reactivity of the β-lactam system and its application in organic synthesis: (e) Marihas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
11. 4. Some recent examples on the use of radical reactions to build β-lactam antibiotics: (a) Alcaide, B.; Moreno, A. M.; Rodríguez-Vicente; Sierra, M. A. Tetrahedron:Asymmetry 1996, 7, 2203.
12. (b) Banik, B. K.; Subbaraju, G. V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363.
13. (c) Ishibashi, H.; Kamekoa, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489.
14. (d) Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J Org. Chem. 1995, 60, 8403.
15. (e) Alcaide, B.; Benito, J. L.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A.; Sierra, M. A.; García-Granda, S.; Gutierrez-Rodríguez, A. Tetrahedron:Asymmetry 1995 6, 1055.
16. (f) Bosch, E.; Bachi, M. D. J. Org. Chem. 1993, 58, 5581.
17. 5. The aryl-aryl radical coupling has been used to prepare different polycyclic systems. For some examples, see: (a) da Mata, M. L. E. N.; Motherwell, W. B.; Ujjainwall, F. Tetrahedron Lett., 1997, 38, 141.
18. (b) da Mata, M. L. E. N.; Motherwell, W. B.; Ujjainwall, F. Tetrahedron Lett., 1997, 38, 137.
19. (c) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S.; Pereira, A. Tetrahedron 1997, 53, 269.
20. (d) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S.; Tetrahedron 1997, 53, 285.
21. (e) Motherwell, W. B.; Pennell, A. M. K. J. Chem. Soc., Chem. Commun. 1991, 877.
22. (f) Togo, H.; Kikuchi, O. Tetrahedron Lett. 1988, 29, 4133.
23. 6. The importance of molecules possessing the biaryl unit as a central feature has been widely recognized. See, for example: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. Int. Ed. Engl. 1990, 29, 977.
24. 7. The stereochemistry observed for these reactions was expected according to the current model for the Staüdinger reaction. See, for example: Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers Inc., New York, 1993; Ch. 6, p 295.
25. 3SnH was added. The mixture was refluxed until complete dissapareance of the starting product (t.l.c.). It is notable that slow addition (syringe pump) was no required for these reactions.
26. 9. Compounds 2a-c are, formally, phenanthridine derived 2-azetidinones. In fact, the reaction of phenanthridine and different ketenes gave condensed biaryl-2-azetidinones related to 2. These results fell out the scope of this paper and will be published in due time.
27. 10. The chemistry of related 1-amidoalkyl radicals have been reviewed. See, for instance: Renaud, Ph.; Giraud, L. Synthesis, 1996, 913.
28. For recent papers, see: (a) Quirante, J.; Escolano, C.; Bonjoch, J. Synlett. 1997, 179.
29. (b) Stojanovic, A.; Renaud, Ph. Synlett. 1997, 181.
30. 11. Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163, and references cited therein.
31. 12. Joyeau, R.; Yadav, L. D. S.; Wakselman, M. J. Chem. Soc., Perkin Trans, 1 1987, 1899.