Kinugasa reaction under click chemistry conditions

Synlett

Volumn , Issue 10, 2007, Pages 1585-1588

  Basak, A ^a   Chandra, K ^a   Pal, R ^a   Ghosh, S C ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

lactam; Click chemistry; Kinugasa reaction; Nitrone

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; KINUGASA REACTION;

EID: 34347366362     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980383     Document Type: Article

References (39)

1. (a) Chemistry and Biology of β-Lactam Antibiotics, Vol. 1; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
2. (b) Chemistry and Biology of β-Lactam Antibiotics, Vol. 2; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
3. (c) Chemistry and Biology of β-Lactam Antibiotics, Vol. 3; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
4. (d) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman & Hall: London, 1992.
5. (e) Antibiotics Containing the β-Lactam Structure, Part 1; Demain, A. L.; Solomon, N. A., Eds.; Springer: Berlin, 1983.
6. (f) Antibiotics Containing the β-Lactam Structure, Part 2; Demain, A. L.; Solomon, N. A., Eds.; Springer: Berlin, 1983.
7. (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226.
8. (b) Alcaide, B.; Almendros, P. Synlett 2002, 381.
9. (c) Alcaide, B.; Almendros, P. Curr. Med. Chem. 2004, 11, 1921.
10. (d) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
11. (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837.
12. Kinugasa, M.; Hashimoto, S. J. Chem. Soc., Chem. Commun. 1972, 466.
13. (a) Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
14. (b) Shintani, R.; Fu, G. C. Angew. Chem. Int. Ed. 2003, 42, 4082;
15. Angew. Chem. 2003, 115, 4216.
16. (a) Basak, A.; Bdour, H. M.; Bhattacharya, G. Tetrahedron Lett. 1997, 38, 2535.
17. (b) Basak, A.; Bhattacharya, G.; Bdour, H. M. M. Tetrahedron 1998, 54, 6529.
18. (c) Basak, A.; Ghosh, S. C.; Bhowmick, T.; Das, A. K.; Bertolasi, V. Tetrahedron Lett. 2002, 43, 5499.
19. (d) Basak, A.; Ghosh, S. C. Synlett 2004, 1637.
20. (e) Basak, A.; Pal, R. Bioorg. Med. Chem. Lett. 2005, 15, 2015.
21. Contelles, J. M. Angew. Chem. Int. Ed. 2004, 43, 2198.
22. Ding, L. K.; Irwin, W. J. J. Chem. Soc., Perkin Trans. 1 1976, 2382.
23. (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
24. (b) Borman, S. Chem. Eng. News 2002, 80, 29.
25. (c) Demko, Z. P.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2113.
26. (d) Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
27. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
28. (b) Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem. Int. Ed. 2005, 44, 2210.
29. (a) Ye, M.-C.; Zhou, J.; Huang, Z.-Z.; Tang, Y. Chem. Commun. 2003, 2554.
30. (b) Ye, M. C.; Zhou, J.; Tang, Y. J. Org. Chem. 2006, 71, 3576.
31. (a) Guo, L.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. J. Chem. Soc., Chem. Commun. 1994, 243.
32. (b) Menger, F. M.; Chen, X. Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. J. Am. Chem. Soc. 1993, 115, 6600.
33. (a) All the nitrones were prepared according to the procedure described in: Bhattacharya, G. PhD Thesis; Indian Institute of Technology: Kharagpur, India, 1997.
34. 1H NMR: δ = 7.15 (dd, J = 4.0, 4.8 Hz, 1 H), 7.39-7.56 (m, 5 H), 7.76-7.81 (m, 2 H), 8.46 (s, 1 H).
35. 14 in quantitative yield.
36. Dess, D. B.; Martin, J. C. J. Am Chem. Soc. 1991, 113, 7277.
37. The spectral data for all the known compounds have been reported: (a) Basak, A.; Rudra, K. R.; Ghosh, S. C.; Bhattacharya, G. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40, 974.
38. (b) Ghosh, S. C. PhD Thesis; Indian Institute of Technology: Kharagpur, India, 2005.
39. +].