New application of Pictet-Spengler reaction leading to the synthesis of an unusual seven-membered heterocyclic ring system

Journal of Organic Chemistry

Volumn 70, Issue 12, 2005, Pages 4889-4892

  Kundu, Bijoy ^a   Sawant, Devesh ^a   Partani, Pankaj ^a   Kesarwani, Amit P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; CHEMICAL BONDS; IONS; SYNTHESIS (CHEMICAL);

ALIPHATIC AMINES; AMINE FUNCTIONALITY; IMIDAZOLES; PICTET-SPENGLER REACTIONS;

REACTION KINETICS;

ALDEHYDE; AROMATIC AMINE; AZULENE DERIVATIVE; CARBON; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NITROGEN;

ARTICLE; CATALYSIS; CHEMICAL BOND; PICTET SPENGLER REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION; SUBSTITUTION REACTION;

EID: 20344383734     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050384h     Document Type: Article

References (46)

1. Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030-2036.
2. For reviews, see: (a) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311-2352.
3. (b) Nielsen, T. E.; Diness, F.; Meldal, M. Curr. Opin. Drug. Discuss. Dev. 2003, 6, 801-814.
4. (c) Cox, E. D.; Cook, J. Chem. Rev. 1995, 95, 1797-1842.
5. (d) Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 151-190.
6. (a) Beke, G.; Szabo, L. F.; Podanyi, B. J. Nat. Prod. 2002, 65, 649-655.
7. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868.
8. (c) Kametani, T.; Koizumi, M.; Okui, K.; Nishii, Y.; Ono, M. J. Med. Chem. 1972, 15, 203-204.
9. (d) Stocker, F. B.; Fordice, M. W.; Larson, J. K.; Thorstenson, J. H. J. Org. Chem. 1966, 31, 2380-2383.
10. (e) Heyl, D.; Harris, S. A.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 3429-3431.
11. (f) Kametani, T.; Fukumoto, K. Heterocycles 1975, 3, 311-318.
12. (a) Gonzalez, J. F.; Cuesta, E.; Avendano, C. Tetrahedron 2004, 60, 6319-6326.
13. (b) Yu, J.; Wearing, X. Z.; Cook, J. M. Tetrahedron Lett. 2003, 44, 543-547.
14. (c) Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58, 1471.
15. (d) Singh, K.; Deb, P. K.; Venugopalan, P. Tetrahedron 2001, 57, 7939-7949.
16. (e) Cox, E. D.; Hamaker, L. K.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44-61.
17. (f) Kametani, T.; Iida, H.; Shinbo, M.; Endo, T. Chem. Pharm. Bull. 1968, 16, 949-952.
18. (g) Kametani, T.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H. J. Chem. Soc. C 1971, 2632-2634.
19. (h) Stuart, K.; Woo-Ming, R. Heterocycles 1975, 3, 223-264.
20. (i) Von Strandtmann, M.; Puchalski, C.; Shavel, J. J. Med. Chem. 1964, 7, 141-146.
21. (j) Brown, R. T.; Chappie, C. L. J. Chem. Soc., Chem. Commun. 1973, 886-888.
22. (k) Srinivasan, N.; Ganesan, A. J. Chem. Soc., Chem. Commun. 2003, 916-917.
23. (l) Tsuji, R.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2003, 14, 177-180.
24. (m) Jiang, W.; Sui, Z.; Chen, X. Tetrahedron Lett 2002, 43, 8941-8945.
25. (n) Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65, 4685-4693.
26. (o) Yamada, H.; Kawate, T.; Matsumizu, M.; Nishida, A.; Yamaguchi, K.; Nakgawa, M. J. Org. Chem. 1998, 63, 6348-6354.
27. (p) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 11865-11884.
28. (q) Feng, X.; Lancelot, J. C.; Gillard, A. C.; Landelle, H.; Rault, S. J. Heterocycl. Chem. 1998, 35, 1313-1316.
29. (r) Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Sridharan, V.; Suganthan, S.; Pett, M. T.; Zhang, J. Tetrahedron 2000, 56, 6585-6594.
30. (s) Ducrot, P.; Rabhi, C., Thal, C. Tetrahedron 2000, 56, 2683-2692.
31. (a) Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Nu, G. S.; Yamanaka, E.; Hutchkins, L.; DiPierro, M.; Cook, J. M. J. Org. Chem. 1979, 44, 535-545.
32. (b) Sandrin, J.; Soerens, D.; Mokry, P.; Cook, J. M. Heterocycles 1977, 6, 1133-1139.
33. (c) Dai, W. M.; Zhu, H. J.; Hao, X. J. Tetrahedron Lett 1996, 37, 5971-5974.
34. (d) Czerwinski, K. M.; Deng, L.; Cook, J. M. Tetrahedron Lett. 1994, 33, 4721-4724.
35. (e) Zhang, L. H.; Bi, Y. Z.; Yu, F. X.; Menzia, G.; Cook, J. M. Heterocycles 1992, 34, 517-547.
36. (f) Ungemach, F.; DiPierro, M.; Weber, R.; Cook, J. M. J. Org. Chem. 1981, 46, 164-168.
37. (g) Jawdosiuk, M.; Cook, J. M. J. Org. Chem. 1984, 49, 2699-2701.
38. (h) Bonnet, D.; Ganesan A. J. Comb. Chem. 2002, 4, 546-548.
39. (i) Wang, H.; Ganesan, A. Org Lett 1999, 1, 1647-1649.
40. (j) Zawadzka, A.; Leniewski, A.; Maurin, J. K.; Wojtasiewicz, K.; Czarnocki, Z. Org. Lett. 2001, 3, 997-999.
41. (k) Gremmen, C.; Wanner, M. J.; Koommen, G. J. Tetrahedron Lett. 2001, 42, 8885-8888.
42. (l) Gremmen, C.; Willemse, B.; Wanner, M. J.; Koomen G. J. Org. Lett. 2000, 2, 1955-1958.
43. Kundu, B.; Sawant, D.; Chhabra, R. J. Comb. Chem. 2005, 7, 317-321.
44. (a) Pokk, P.; Zharkovsky, A. J. Physiol. Pharmacol. 1997, 48, 253-61.
45. (b) Hashimoto, K.; Inoue, O.; Goromaru, T.; Yamasaki, T. Int. J. Rad. Appl. Instrum. B. 1988, 15, 637-44.
46. Liiberatore, A.-M.; Schulz, J.; Pommier, J.; Barthelemy, M.-A.; Huchet, M.; Chabrier, P.-E.; Bigg, D. Bioorg. Med. Chem. Lett. 2004, 14, 3521-3523.