Parallel synthesis of 1,2,3,4-tetrahydro-β-carbolines using microwave irradiation

Synlett

Volumn , Issue 10, 2002, Pages 1709-1711

  Wu, Cheng Yi ^a   Sun, Chung Ming ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

1,2,3,4 tetrahydro carbolines; Combinatorial chemistry; Liquid phase method; Microwave assisted combinatorial synthesis; Scaffold

Indexed keywords

ALDEHYDE; CARBOLINE DERIVATIVE; KETONE; POLYMER; TRYPTOLINE DERIVATIVE; TRYPTOPHAN DERIVATIVE;

ARTICLE; CHEMICAL BINDING; IMMOBILIZATION; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PURIFICATION; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036400027     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34220     Document Type: Article

References (37)

1. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. (b) Dolle, R. E. J. Comb. Chem. 2001, 3, 477.
3. (a) Sun, C. M. Comb. Chem. High Throllghput Screening 1999, 2, 299.
4. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
5. (c) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem.-Eur. J. 2000, 6, 133.
6. (d) Reggelin, M.; Brenig, V.; Zur, C. Org. Lett. 2000, 2, 531.
7. (a) Pan, P. C.; Sun, C. M. Tetrahedron Lett. 1998, 39, 9505.
8. (b) Shey, J. Y.; Sun, C. M. Synlett 1998, 1423.
9. (c) Shey, J. Y.; Sun, C. M. J. Comb. Chem. 1999, 1, 361.
10. (d) Yeh, C. M.; Tung, C. L.; Sun, C. M. J. Comb. Chem. 2000, 2, 341.
11. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
12. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
13. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
14. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
15. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
16. For reviews of microwave-assisted reactions in solution phase and solvent free condition: (a) Caddick, S. Tetrahedron 1995, 51, 10403. (b) Galema, S. A. Chem. Soc. Rev. 1997, 26, 233. (c) Varma, R. S. Green Chem. 1999, 1, 43. (d) Ranu, B. C.; Guchhait, S. K.; Ghosh, K.; Patre, A. Green Chem. 2000, 2, 5. (e) Loupy, A.; Perreux, L. Tetrahedron 2001, 57, 9199. (f) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
17. Microwave-assisted solid-phase combinatorial synthesis: (a) Nielsen, J.; Hoel, A. M. L. Tetrahedron Lett. 1999, 40, 3941. (b) Chandrasskhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597. (c) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (d) Brain, C. T.; Brunton, S. A. Synlett 2001, 382. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95.
18. Microwave-assisted solid-phase combinatorial synthesis: (a) Nielsen, J.; Hoel, A. M. L. Tetrahedron Lett. 1999, 40, 3941. (b) Chandrasskhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597. (c) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (d) Brain, C. T.; Brunton, S. A. Synlett 2001, 382. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95.
19. Microwave-assisted solid-phase combinatorial synthesis: (a) Nielsen, J.; Hoel, A. M. L. Tetrahedron Lett. 1999, 40, 3941. (b) Chandrasskhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597. (c) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (d) Brain, C. T.; Brunton, S. A. Synlett 2001, 382. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95.
20. Microwave-assisted solid-phase combinatorial synthesis: (a) Nielsen, J.; Hoel, A. M. L. Tetrahedron Lett. 1999, 40, 3941. (b) Chandrasskhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597. (c) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (d) Brain, C. T.; Brunton, S. A. Synlett 2001, 382. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95.
21. Microwave-assisted solid-phase combinatorial synthesis: (a) Nielsen, J.; Hoel, A. M. L. Tetrahedron Lett. 1999, 40, 3941. (b) Chandrasskhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597. (c) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (d) Brain, C. T.; Brunton, S. A. Synlett 2001, 382. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95.
22. Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406.
23. (a) Hermkens, P. H. H.; Plate, R.; Kruse, C. G.; Scheeren, H. W.; Ottenheijm, H. C. J. J. Org. Chem. 1992, 57, 3881.
24. (b) Chi, D. Y.; O'Neil, J. P.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A. J. Med. Chem. 1994, 37, 928.
25. (c) Leteurtre, F.; Sackett, D. L.; Madalengoitia, J.; Kohlhagan, G.; Macdonald, T. L.; Hamel, E.; Paull, K. D.; Pommier, Y. Bioochem. Pharmacol. 1995, 19, 128.
26. (d) Cui, C. B.; Kakeya, H.; Osada, A. Tetrahedron 1997, 53, 59.
27. Solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633. (b) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291. (c) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737. (d) Wuang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647. (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
28. Solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633. (b) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291. (c) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737. (d) Wuang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647. (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
29. Solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633. (b) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291. (c) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737. (d) Wuang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647. (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
30. Solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633. (b) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291. (c) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737. (d) Wuang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647. (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
31. Solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633. (b) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291. (c) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737. (d) Wuang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647. (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
32. (a) Bose, A. K.; Maghar, S. M.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968.
33. (b) Sanchez-Sancho, F.; Mann, Z.; Herrado, B. Synlett 2000, 509.
34. The cyclization reaction of Trp-Wang resin with benzaldehyde (10 equiv) was complete at 80 °C in toluene for overnight. See: Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041.
35. 2 258.1358. Found: 258.1360.
36. 13C NMR spectroscopy) for C-1 and C-3 in trans-isomers were more upfield compared to those of cis-isomers. See: (a) Ungemach, F.; Soerens, D.; Weber, R.; DiPierro, M.; Campos, P.; Mokry, P.; Cook, J. M.; Silvertoon, J. V. J. Am. Chem. Soc. 1980, 102, 6976. (b) An excellent review for the Pictet-Spengler reaction: Cox, E.; Cook, J. M. Chem. Rev. 1995, 95, 179.
37. 13C NMR spectroscopy) for C-1 and C-3 in trans-isomers were more upfield compared to those of cis-isomers. See: (a) Ungemach, F.; Soerens, D.; Weber, R.; DiPierro, M.; Campos, P.; Mokry, P.; Cook, J. M.; Silvertoon, J. V. J. Am. Chem. Soc. 1980, 102, 6976. (b) An excellent review for the Pictet-Spengler reaction: Cox, E.; Cook, J. M. Chem. Rev. 1995, 95, 179.