Cycloaddition reaction of Schiff bases with ketenes generated by pyrolysis of 2-aryl-substituted 1,5,7-trioxaspiro[2.5]octane-4,8-diones

Journal of Heterocyclic Chemistry

Volumn 43, Issue 1, 2006, Pages 21-28

  Tsuno, Takashi ^a   Kondo, Kosuke ^a   Sugiyama, Kunio ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,5,7 TRIOXASPIRO[2.5]OCTANE 4,8 DIONE DERIVATIVE; 2 AZA 5,7 DIOXASPIRO[3.4]OCTANE 1,8 DIONE; 2 BENZYLOXY 1,4 DIPHENYL BETA LACTAM 3 CARBOXYLIC ACID; ALPHA OXO KETENE; CARBOXYLIC ACID DERIVATIVE; KETENE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; HYDROGENATION; PYROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 30944462968     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430104     Document Type: Article

References (52)

1. M. A. A. Gaber and H. McNab, Synthesis, 2059 (2001).
2. B.-C. Chen, Heterocyles, 32, 529 (1991).
3. M. F. Strozhev, I. Z. Lielbriridis and O. I. Neilands, Khim. Geterotskl. Soedin., 579 (1991);
4. H. McNab, Chem. Soc. Rev. 7, 345 (1978).
5. T. Tsuno, K. Sugiyama and H. Ago, Heterocyles, 38, 2631 (1994);
6. T. Tsuno and K. Sugiyama, Heterocycles, 30, 1581 (1990).
7. T. Tsuno and K. Sugiyama, Trends Heterocylic Chem., 7, 91 (2001);
8. T. Tsuno and K. Sugiyama, Bull. Chem. Soc. Jpn., 68, 3175 (1995);
9. T. Tsuno and K. Sugiyama, Heterocycles, 38, 859 (1994);
10. T. Tsuno and K. Sugiyama, Tetrahedron Lett., 33, 2829 (1992);
11. T. Tsuno and K. Sugiyama, Heterocycles, 32, 1989 (1991);
12. T. Tsuno and K. Sugiyama, Chem. Lett., 503 (1990).
13. R. F. C. Brown, F. W. Eastwood and K. Harrington, Aust. J. Chem., 27, 2373 (1974).
14. M. Sato, H. Ogasawara, E. Yoshizumi and T. Kato, Chem. Pharm. Bull., 31, 1902 (1983).
15. S. Hayashi, M. Furukawa, Y. Fujino, H. Okabe and T. Nakao, Chem. Pharm. Bull., 19, 2404 (1971).
16. R. V. Stevens, G. S. Bisacchi, L. Goldsmith and C. E. Strouse, J. Org. Chem., 45, 2708 (1980);
17. M. Farines and J. Soulier, Bull. Chem. Soc. Fr., 332 (1970).
18. Crystallographic data of 3j and 4j have been deposited at the Cambridge Crystallographic Data Centre as CCDC Numbers 197782 and 197783, respectively. Copies of the data can be obtained free of charge upon application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033, e-mail: deposit@ccdc.cam.ac.uk).
19. M. Sato, H. Ban and C. Kaneko, Tetrahedron Lett., 38, 6686 (1997).
20. C. del Pozo, A. Macías, F. López-Ortiz, M. Á. Maestro, E. Alonso and J. González, Eur. J. Org. Chem., 535 (2004).
21. C. Zhou and D. M. Birney, J. Am. Chem. Soc., 124, 5231 (2002).
22. A. Bogdanova and V. V. Popik, J. Am. Chem. Soc., 125, 1415, 14153 (2003);
23. A. Bogdanova and V. V. Popik, J. Am. Chem. Soc., 125, 1456 (2003);
24. R. V. Stevens, G. S. Bisacchi, L. Goldsmith and C.E. Strouse, J. Org. Chem., 45, 2708 (1980).
25. The Organic Chemistry of β-Lactams; G. I. Georg, ed.; VCH: New York, 1993.
26. P, Claudio, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Eur. J. Org. Chem., 3223 (1999).
27. J. C. Sheehan and E. J. Corey, Org. React. 9, 388 (1957).
28. Recent publications for Staudinger reaction, see: A. L. Ahaikh, V. G. Puranik and A. R. A. S. Deslimukh, Tetrahedron, 61, 2441 (2005);
29. L. Yong, L. Jiao and X. J. Shiwei, J. Org. Chem., 70, 334 (2005);
30. B. K. Banik, I. Banik and F. F. Becker, Bioorg. Med. Chem., 13, 3611 (2005);
31. A. Macias, W. Alonso, C. Del Pozo, A. Venturini and J. Gonzalez, J. Org. Chem. 69, 7004 (2004);
32. M. Arum, S. N. Joshi, V. G. Puranik, B. M. Bhawal and A. R. S. A. Deshmukh, Tetrahedron, 59, 2309 (2003);
33. X. Lin and S. M. Weinreb, Tetrahedron Lett., 42, 2631 (2001).
34. O. Arjona, A. G. Csákÿ, M. C. Murcia and J. Plume, Tetrahedron Lett., 43, 6405 (2002);
35. J. P. N. Papillon and R. J. K. Taylor, Org. Lett., 2, 1987 (2002);
36. F. Toda, H. Miyamoto, M. Inoue, S. Yasaka and I. Matijasic, J. Org. Chem., 65, 2728 (2000);
37. V. Barba, C. Hernández, S. Rojas-Lima, N. Farfán and R. Santillan, Can. J. Chem., 77, 2025 (2000);
38. P. D. Croce and C. La Rosa, Tetrahedron: Asymmetry, 10, 1193 (1999);
39. S. Anklam and J. Liebscher, Tetrahedron, 54, 6369 (1998);
40. A. Strauss and H.-H. Otto, Helv. Chim. Acta, 80, 1823 (1997);
41. S. Ruf and H.-H. Otto, Helv. Chim. Acta, 78, 629 (1995);
42. M. Johner, G. Rihs, S. Gürtler and H.-H. Otto, Helv. Chim. Acta, 77, 2147 (1994);
43. S. Gürtler, M. Johner, S. Ruf and H.-H. Otto, Helv. Chim. Acta, 76, 2958 (1993);
44. S. L. Blanc, J.-P. Pete and O. Piva, Tetrahedron Lett., 33, 1993 (1992).
45. A. Battaglia, E. Baldelli, G. Barbaro, P. Giorgianni, A. Guerrini, M. Monari and S. Selva, Tetrahedron; Asymmetry, 13, 1825 (2002);
46. G. Blay, B. Monje, J. R. Pedro and R. Ruiz, Tetrahedron Lett. 43, 8463 (2002);
47. A. Battaglia, G. Barbaro, P. Giorgianni, A. Guerrini and A. Pepe, Tetrahedron; Asymmetry, 12, 1015 (2001);
48. M. Mitsuya, Y. Ogino, N. Ohtake and T. Mase, Tetrahedron, 56, 9901 (2000);
49. M. Mitsuya, Y. Ogino, K. Kawakami, M. Uchiyama, T. Kimura, T. Numazawa, T. Hasegawa, N. Ohtake, K. Noguchi and T. Mase, Bioorg. Med. Chem., 8, 825 (2000);
50. G. Barbaro, A. Battaglia, A. Guerrini and C. Bertucci, Tetrahedron; Asymmetry, 8, 2527 (1997).
51. M. Sato, Yuki Gosei Kagaku Kyokaishi, 46, 596 (1988);
52. M. Sato, Yakugaku Zasshi, 108, 805 (1988).