Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions
Author(s)
Pablo A. Martínez-Soriano1*,
José R. Macías-Pérez2,
Ana María Velázquez1,
Brígida del Carmen Camacho-Enriquez1,
Gustavo Pretelín-Castillo1,
Mónica B. Ruiz-Sánchez1,
Víctor H. Abrego-Reyes3,
Saúl Villa-Treviño2,
Enrique Angeles1
Affiliation(s)
1 Laboratorio de Química Medicinal y Teórica, Departamento de Ciencias Químicas, FES Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, México. 2 Departamento de Biología celular, Centro de Investigación y Estudios Avanzados, Instituto Politécnico Nacional, México, D.F., México. 3 Qsar Analytics S.A. de C.V. Ciudad Satélite, Naucalpan de Juárez, México.
1 Laboratorio de Química Medicinal y Teórica, Departamento de Ciencias Químicas, FES Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, México. 2 Departamento de Biología celular, Centro de Investigación y Estudios Avanzados, Instituto Politécnico Nacional, México, D.F., México. 3 Qsar Analytics S.A. de C.V. Ciudad Satélite, Naucalpan de Juárez, México.
ABSTRACT
A convenient and easy method is described for the formation of carboxamides from carboxylic acids and primary amines in solventless conditions using infrared (IR) light. Thus, under IR light, cinnamic acid derivatives and amines can produce yields ranging from 50% to 85% of the resulting amide.
A convenient and easy method is described for the formation of carboxamides from carboxylic acids and primary amines in solventless conditions using infrared (IR) light. Thus, under IR light, cinnamic acid derivatives and amines can produce yields ranging from 50% to 85% of the resulting amide.
KEYWORDS
Amides, Carboxylic Acids, Amines, Infrared Light, Solventless, CAPE, CAPA, Cinnamic Acid Analogs
Amides, Carboxylic Acids, Amines, Infrared Light, Solventless, CAPE, CAPA, Cinnamic Acid Analogs
Cite this paper
Martínez-Soriano, P. , Macías-Pérez, J. , Velázquez, A. , Camacho-Enriquez, B. , Pretelín-Castillo, G. , Ruiz-Sánchez, M. , Abrego-Reyes, V. , Villa-Treviño, S. and Angeles, E. (2015) Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions. Green and Sustainable Chemistry, 5, 81-91. doi: 10.4236/gsc.2015.52011.
Martínez-Soriano, P. , Macías-Pérez, J. , Velázquez, A. , Camacho-Enriquez, B. , Pretelín-Castillo, G. , Ruiz-Sánchez, M. , Abrego-Reyes, V. , Villa-Treviño, S. and Angeles, E. (2015) Solvent-Free Synthesis of Carboxylic Acids and Amide Analogs of CAPE (Caffeic Acid Phenethyl Ester) under Infrared Irradiation Conditions. Green and Sustainable Chemistry, 5, 81-91. doi: 10.4236/gsc.2015.52011.
References
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http://dx.doi.org/10.1002/ptr.2594 [2] Natarajan, K., Singh, S., Burke, T.R., Grunberger, D. and Aggarwal, B.B. (1996) Caffeic Acid Phenethyl Ester Is a Potent and Specific Inhibitor of Activation of Nuclear Transcription Factor NF-Kappa B. Proceedings of the National Academy of Sciences of the United States of America, 93, 9090-9095.
http://dx.doi.org/10.1073/pnas.93.17.9090 [3] Orban, Z., Mitsiades, N., Burke, T.R., Tsokos, M. and Chrousos, G.P. (2000) Caffeic Acid Phenethyl Ester Induces Leukocyte Apoptosis, Modulates Nuclear Factor-Kappa B and Suppresses Acute Inflammation. Neuroimmunomodulation, 7, 99-105.
http://dx.doi.org/10.1159/000026427 [4] Huang, M.T., Ma, W., Yen, P., Xie, J.G., Han, J., Frenkel, K., Grunberger, D. and Conney, A.H. (1996) Inhibitory Effects of Caffeic Acid Phenethyl Ester (CAPE) on 12-O-Tetradecanoylphorbol-13-Acetate-Induced Tumor Promotion in Mouse Skin and The Synthesis of DNA, RNA and Protein in Hela Cells. Carcinogenesis, 17, 761-765.
http://dx.doi.org/10.1093/carcin/17.4.761 [5] Huang, M.T., Smart, R.C., Wong, C.Q. and Conney, A.H. (1988) Inhibitory Effect of Curcumin, Chlorogenic Acid, Caffeic Acid, and Ferulic Acid on Tumor Promotion in Mouse Skin by 12-O-Tetradecanoylphorbol-13-Acetate. Cancer Research, 48, 5941-5946. [6] Rajan, P., Vedernikova, I., Cos, P., Berghe, D.V., Augustyns, K. and Haemers, A. (2001) Synthesis and Evaluation of Caffeic Acid Amides as Antioxidants. Bioorganic & Medicinal Chemistry Letters, 11, 215-217.
http://dx.doi.org/10.1016/S0960-894X(00) 00630-2 [7] Naito, Y., Sugiura, M., Yamaura, Y., Fukaya, C., Yokoyama, K., Nakagawa, Y., Ikeda, T., Senda, M. and Fujita, T. (1991) Quantitative Structure-Activity Relationship of Catechol Derivatives Inhibiting 5-Lipoxygenase. Chemical and Pharmaceutical Bulletin, 39, 1736-1745.
http://dx.doi.org/10.1248/cpb.39.1736 [8] Son, S. and Lewis, B.J. (2002) Free Radical Scavenging and Antioxidative Activity of Caffeic Acid Amide and Ester Analogues: Structure-Activity Relationship. Journal of Agricultural and Food Chemistry, 50, 468-472.
http://dx.doi.org/10.1021/jf010830b [9] Nishioka, T., Watanabe, J., Kawabata, J. and Niki, R. (1997) Isolation and Activity of N-p-Coumaroyltyramine, an α- Glucosidase Inhibitor in Welsh Onion (Allium fistulosum). Bioscience, Biotechnology, and Biochemistry, 61, 1138- 1141.
http://dx.doi.org/10.1271/bbb.61.1138 [10] Macias-Perez, J.R., Beltrán-Ramírez, O., Vásquez-Garzón, V.R., Salcido-Neyoy, M.E., Martínez-Soriano, P.A., Ruiz-Sanchez, M.B., ángeles E. and Villa-Trevino, S. (2013) The Effect of Caffeic Acid Phenethyl Ester Analogues in a Modified Resistant Hepatocyte Model. Anti-Cancer Drugs, 24, 394-405.
http://dx.doi.org/10.1097/CAD.0b013e32835e9743 [11] Plagens, A. and Laue, T. (2005) Named Organic Reactions. 2nd Edition, John Wiley & Sons, New York, 320. [12] Wolff, H. (1946) The Schmidt Reaction. Organic Reactions, 3, 307-336. [13] Chandrasekhar, S. and Gopalaiah, K. (2003) Ketones to Amides via a Formal Beckmann Rearrangement in “One Pot”: A Solvent-Free Reaction Promoted by Anhydrous Oxalic Acid. Possible Analogy with the Schmidt Reaction. Tetrahedron Letters, 44, 7437-7439.
http://dx.doi.org/10.1016/j.tetlet.2003.08.038 [14] Yadav, J.S., Reddy, B.V.S., Reddy, U.V.S. and Praneeth, K. (2008) Azido-Schmidt Reaction for the Formation of Amides, Imides and Lactams from Ketones in the Presence of FeCl3. Tetrahedron Letters, 49, 4742-4745.
http://dx.doi.org/10.1016/j.tetlet.2008.05.113 [15] Lee, H.-L. and Aubé, J. (2007) Intramolecular and Intermolecular Schmidt Reactions of Alkyl Azides with Aldehydes. Tetrahedron, 63, 9007-9015.
http://dx.doi.org/10.1016/j.tet.2007.05.079 [16] Liang, J., Jing, L. and Shang, Z.C. (2011) Metal-Free Synthesis of Amides by Oxidative Amidation of Aldehydes with Amines in PEG/Oxidant System. Tetrahedron, 67, 8532-8535.
http://dx.doi.org/10.1016/j.tet.2011.08.091 [17] Zhang, M. and Wu, X.F. (2013) Zinc(II)-Catalyzed Oxidative Amidation of Arylaldehydes with Alkylamines under Solvent-Free Conditions. Tetrahedron Letters, 54, 1059-1062.
http://dx.doi.org/10.1016/j.tetlet.2012.12.010 [18] Suto, Y., Yamagiwa, N. and Torisawa, Y. (2008) Pd-Catalyzed Oxidative Amidation of Aldehydes with Hydrogen Peroxide. Tetrahedron Letters, 49, 5732-5735.
http://dx.doi.org/10.1016/j.tetlet.2008.07.075 [19] Organic Chemistry Portal 2008.
www.organic-chemistry.org [20] Strukil, V., Bartolec, B., Portada, T., Dilovic, I., Halasz, I. and Margetic, D. (2012) One-Pot Mechanosynthesis of Aromatic Amides and Dipeptides from Carboxylic Acids and Amines. Chemical Communications, 48, 12100-12102. [21] Gooben, L.J., Ohlmann, D.M. and Lange, P.P. (2009) The Thermal Amidation of Carboxylic Acids Revisited. Synthesis, 2009, 160-164.
http://dx.doi.org/10.1055/s-0028-1083277 [22] Hosseini, M., Sodagar, E. and Doroodmand, M.M. (2011) Nano Sulfated Titania as Solid Acid Catalyst in Direct Synthesis of Fatty Acid Amides. The Journal of Organic Chemistry, 76, 2853-2859.
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