Efficient synthesis of new N-benzyl- or N-(2-furylmethyl)cinnamamides promoted by the 'green' catalyst boric acid, and their spectral analysis

Synthesis

Volumn , Issue 3, 2008, Pages 0377-0382

  Barajas, José Gregorio Hernández ^a   Méndez, Leonor Yamile Vargas ^a   Kouznetsov, Vladimir V ^a   Stashenko, Elena E ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

Amidation; Amides; Carboxylic acids; Catalysis; N benzylamides

Indexed keywords

BORIC ACID; CINNAMIC ACID; N-(2-FURYLMETHYL)CINNAMAMIDES;

CATALYST ACTIVITY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

3 PHENYL N (1 PHENYLETHYL)PROP 2 ENAMIDE; 3 PHENYL N 4 TOLYLPROP 2 ENAMIDE; AMIDE; BORIC ACID; N (2 FURYLMETHYL)CINNAMAMIDE DERIVATIVE; N (4 CHLOROBENZYL) 3 PHENYLPROP 2 ENAMIDE; N (4 FLUOROBENZYL) 3 PHENYLPROP 2 ENAMIDE; N (4 METHOXYBENZYL) 3 PHENYLPROP 2 ENAMIDE; N BENZYL 3 PHENYLPROP 2 ENAMIDE; N BENZYL CINNAMAMIDE DERIVATIVE; N BENZYL N METHYL 3 PHENYLPROP 2 ENAMIDE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROMETRY; SPECTROSCOPY; STOICHIOMETRY; SYNTHESIS;

EID: 39349107729     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032039     Document Type: Article

References (30)

1. Chalis, M. S.; Butler, A. R. In The Chemistry of the Amino Group; Patai, S., Ed.; Wiley: New York, 1968, 279.
2. For the biological activity, see: (a) Kleemann, A.; Engel, J. Pharmaceutical Substances; Thieme: New York, 1999.
3. (b) Balsamo, A.; Barili, P. L.; Crotti, P.; Macchia, B.; Macchia, F.; Pecchia, A. J. Med. Chem. 1975, 18, 842.
4. (c) Balsamo, A.; Barili, P. L.; Crotti, P.; Macchia, B.; Macchia, F. J. Med. Chem. 1977, 20, 48.
5. (d) Balsamo, A.; Crotti, P.; Lapucci, A.; Macchia, B.; Macchia, F. J. Med. Chem. 1981, 24, 525.
6. For structural studies, see: (a) Kruk, C.; Speargaren, K. Spectrochim. Acta, Part A 1971, 27, 77.
7. (b) Lewis, F. D.; Elbert, J. E.; Upthagrove, A. L.; Hale, P. D. J. Am. Chem. Soc. 1988, 110, 5191.
8. (c) Lewis, F. D.; Elbert, J. E.; Upthagrove, A. L.; Hale, P. D. J. Org. Chem. 1991, 56, 553.
9. For synthetic applications, see: (a) Klemm, L. H.; McGuire, T. M.; Gopinath, K. W. J. Org. Chem. 1976, 41, 2571.
10. (b) Bernini, R.; Cachia, S.; De Salve, I.; Fabrizi, G. Synlett 2006, 2947.
11. (c) Nair, V.; Mohanan, K.; Suja, T. D.; Biju, A. Synthesis 2007, 1179.
12. Carey, J. S.; Laffan, D.; Thomon, C.; Williams, M. K. Org. Biomol. Chem. 2006, 4, 2337.
13. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001, 506-508.
14. Gelens, E.; Smeets, L.; Sliedregt, L.; Van Steen, B.; Kruse, C.; Leurs, R.; Orru, R. V. A. Tetrahedron Lett. 2005, 46, 3751.
15. Prasad, A. K.; Husain, M.; Singh, B. K.; Gupta, R. K.; Manchanda, V. K.; Olsen, C. E.; Parmar, S. V. Tetrahedron Lett. 2005, 46, 4511.
16. Sharghi, H.; Sarvari, M. H. Tetrahedron 2002, 58, 10323.
17. Sabot, C.; Kamur, K. A.; Meunier, S.; Mioskowski, C. Tetrahedron Lett. 2007, 48, 3863.
18. Tang, P. Org. Synth. 2005, 81, 262.
19. Maki, T.; Ishihara, K.; Yamamoto, H. Tetrahedron 2007, 63, 8645.
20. Houston, T. T.; Wilkinson, B. L.; Blanchfield, J. T. Org. Lett. 2004, 6, 681.
21. Vargas, M. L. Y.; Castelli, M. V.; Kouznetsov, V. V.; Urbina, G. J. M.; López, S. N.; Sortino, M.; Enriz, R. D.; Ribas, J. C.; Zacchino, S. A. Bioorg. Med. Chem. 2003, 11, 1531.
22. Kouznetsov, V. V.; Rivero Castro, J.; Ochoa Puentes, C.; Stashenko, E. E.; René Martinez, J.; Ochoa, C.; Montoro Pereira, D.; Nogal Ruiz, J. J.; Fernández Portillo, C.; Muelas Serrano, S.; Gómez Barrio, A.; Bahsas, A.; Amaro-Luis, J. Arch. Pharm. 2005, 338, 32.
23. Suvire, D. F.; Sortino, M.; Kouznetsov, V. V.; Vargas, M. L. Y.; Zacchino, S. A.; Mora Cruz, U.; Enriz, R. D. Bioorg. Med. Chem. 2006, 14, 1851.
24. Collum, D. B.; Chen, S.-C.; Ganem, B. J. Org. Chem. 1978, 43, 4393.
25. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.
26. Huang, Z.; Reilly, J. E.; Buckle, R. N. Synlett 2007, 1026.
27. Paulsen, H.; Todt, K. Angew. Chem., Int. Ed. Engl. 1966, 5, 899.
28. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994, 620.
29. The boric acid promoted azeotropic reflux procedure seems not to be limited to cinnamic acid or its derivatives; see refs. 11 and 13.
30. Compounds 3c, 3g, and 3j displayed antifungal activity, especially 3c, which showed to be a moderate antifungal agent for three different dermatophytic pathogenic fungi stumps. All the evaluated products (3a-j) possessed poor anti-AChE activity. These results will be published elsewhere.