Role of the acid group in the Pictet-Spengler reaction of α-amino acids

Synlett

Volumn , Issue 12, 2006, Pages 1903-1907

  De La Figuera, Natalia ^a   Fiol, Sandra ^a   Fernández, Joan Carles ^a   Forns, Pilar ^a   Fernández Forner, Dolors ^a   Albericio, Fernando ^b  

^a Barcelona Science Park ^*  (Spain)

^b INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

Author keywords

Alcoholic solvents; Amino acids; Dopa; Free acid; Histidine; Microwave; Mild conditions; Phenylalanine; Pictet Spengler

Indexed keywords

ALCOHOL; ALPHA AMINO ACID; ANISALDEHYDE; BENZALDEHYDE; DOPA; HISTIDINE; PHENYLALANINE;

ARTICLE; MICROWAVE IRRADIATION; PICTET SPENGLER REACTION;

EID: 33747053929     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948170     Document Type: Article

References (31)

1. Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030.
2. Whaley, W. M.; Govindachari, T. R. In Organic Reactions, Vol. 4; Adams, R., Ed.; John Wiley and Sons: New York, 1951, 151.
3. Konda, M.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1975, 23, 1063.
4. Konda, M.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1977, 25, 69.
5. Tatsui, G. J. Pharm. Soc. Jpn. 1928, 48, 92.
6. (a) Hamaguchi, F.; Nagasaka, T.; Ohki, S. Yakugaku Zasshi 1974, 94, 351.
7. (b) Stuart, K.; Woo-Ming, R. Heterocycles 1975, 3, 223.
8. (c) Bergman, J. Acta Chem. Scand. 1971, 25, 3296.
9. (d) Strandtmann, M.; Puchalski, C.; Shavel, J. J. Med. Chem. 1964, 7, 141.
10. (e) Degraw, J.; Kennedy, J. G.; Skinner, W. A. J. Med. Chem. 1967, 10, 127.
11. (f) Julia, M.; Bagot, J.; Siffert, O. Bull. Soc. Chim. Fr. 1973, 1424.
12. (g) Brown, R. T.; Chapple, C. L. J. Chem. Soc., Chem. Commun. 1973, 886.
13. Grieco, P.; Campiglia, P.; Gomez-Monterrey, I.; Novellino, E. Tetrahedron Lett. 2002, 6297.
14. Beke, G.; Szabó, L. F.; Podányi, B. J. Nat. Prod. 2002, 65, 649.
15. Cox, E.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
16. Jackson, A. H.; Smith, A. E. Tetrahedron 1968, 24, 403.
17. Manini, P.; D'Ischia, M.; Prota, G. J. Org. Chem. 2001, 66, 5048.
18. Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G. S.; Yamanaka, E.; Hutchins, L.; DiPierro, M.; Cook, J. M. J. Org. Chem. 1979, 44, 535.
19. (a) Fodor, G.; Nagubandi, S. Tetrahedron 1980, 36, 1279.
20. (b) Sandrin, J.; Soerens, D.; Mokry, P.; Cook, J. M. Heterocycles 1977, 6, 1133.
21. (c) Zhang, L.; Cook, J. M. Heterocycles 1988, 27, 2759.
22. (d) Behforonz, M.; West, S. J.; Chakrabarty, C.; Dusk, D. A.; Zarrimaye, H. Heterocycles 1992, 48, 1805.
23. (e) Baley, P. D.; Hollinshead, S. P.; McLay, N. R.; Morgan, K.; Palmer, S. J.; Prince, S. N.; Reynolds, C. D.; Wood, S. D. J. Chem. Soc., Perkin Trans. 1 1993, 431.
24. (f) Massiot, G.; Mulamba, T. J. Chem. Soc., Chem. Commun. 1983, 1147.
25. (g) Khnong, Q.; Nemlin, J.; Kervagoret, J.; Pancrazi, A. Tetrahedron 1992, 48, 6689.
26. (h) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron Lett. 1993, 34, 5867.
27. The reaction has been done also with aldehydes containing functionalities such as acetals, esters, amides. These functionalities otherwise not stable to acidic catalyst have been proven to give good yields in these conditions.
28. Bison, G.; Schlupp, J.; Winterscheid, J.; Thewalt, K. US 4791210, 1988; Chem. Abstr. 1987, 109, 73455.
29. +].
30. Guiso, M.; Marra, C.; Cavarischia, C. Tetrahedron Lett. 2001, 42, 6531.
31. Reaction with 3,4-dimethoxy-L-phenylalanine in which the hydroxy groups are methylated and the carboxylic acid is in its free form showed no reaction under these mild conditions. Methoxy groups are less activating than hydroxy groups on aryl systems. It seems that the intramolecular acidic catalysis only promoted reaction for activated systems.