Síntesis del 2-metil-1H-benzo[d]imidazol y 2-etil-1H-benzo[d]imidazol a partir de de L-serina, L-treonina, L-cisteína.
Palabras clave:
2-metilbenzimidazol, 2-etilbenzimidazol, α-aminoácidos, o-fenilendiamina, microondas, RMN
Resumen
El 2-metil-1H-benzo[d]imidazol (5) y 2-etil-1H-benzo[d]imidazol (6) se obtuvieron mediante la reacción de o-fenilendiamina con L-serina, L-cisteina o L-treonina respectivamente. La inducción de la reacción se llevó a cabo mediante el uso de dos metodologías alternativas: Fusión o Radiación de microondas (MW). El uso de dichos procesos sintéticos resulto ser sencillo y eficiente. Sin embargo, es indispensable utilizar las medidas de seguridad adecuadas para llevar a cabo éstas reacciones químicas. La estructura molecular de 5 y 6 se determinó por RMN de 1H, 13C y difracción de rayos-X. El mecanismo de reacción probable que se propone en el presente trabajo involucra la pérdida de agua, cianuro de hidrógeno y migración de átomos de hidrógeno (o del grupo metilo).
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Citas
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Chen, R.-H., Xiong, J.-F., Peng, P., Mo, G.-Z., Tang, X.-S., Wang, Z.-Y., Wang, X.-F., 2014. Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method. Asian J. Chem. 26 (3). 926-932.
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Maekawa, K., Ohtani, J., 1976. Synthese von 2-(1’-Amino-1’-substituiertem alkyl)-benzimidazol aus Aminosuren und Ihre Biologische Aktiviät. Agr. Biol. Chem. 40, 791-799.
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Özgür, D. C., Ümide, D. Ö., Zafer, A. K., Yusuf, Ö., 2009. Effects of Some 1,3,5-Trisubstitued-2-pyrazoline Derivatives on Depression and Anxiety Parameters of Mice. Arch. Pharm. Res. 32 (9), 1293-1299.
Padalkar, V., S., Gupta,V. D., Phatangare, K. R., Patil, V. S., Umape, P. G., Sekar, N., 2012. Indion 190 resin: efficient, environmentally friendly, and reusable catalyst for synthesis of benzimidazoles, benzoxazoles, and benzothiazoles. Green Chem. Lett. Rev. 5 (2), 139-145.
Peng, P., Xiong, J.‑F., Mo, G.‑Z. Zheng, J.‑L., Chen, R.‑H., Chen X.‑Y., Wang, Z.-Y., 2014. A concise synthesis of benzimidazoles via the microwave‑assisted one‑pot batch reaction of amino acids up to a 10‑g scale. Amino Acids 46, 2427-2433.
Phillips, M. A., 1928. CCCXVII-The Formation of 2-Substituted Benziminazoles. J. Chem. Soc. 13, 2393-2399.
Porter, Q. N., Spear, R. J., 1970. Mass Spectrometric Studies-VI: Aziridines.Org. Mass Spectrom. 3, 1259-1282.
Thakuria, H., Das, G., 2008. An expeditious one-pot solvent-free synthesis of benzimidazole derivatives. ARKIVOK 321-328.
Thompson, J. R., Ovens, J. S., Williams, V. E., Leznoff, D. B., 2013. Supramolecular Assembly of Bis(benzimidazole)pyridine: An Extended Anisotropic Ligand For Highly Birefringent Materials. Chem. Eur. J. 19, 16572-16578.
Wenker, H., 1935. The Preparation of Ethylene Imine from Monoethanolamine. J. Am. Chem. Soc. 57 (11), 2328-2328.
Akram, M., Asif, H. M., Uzair, M., Akhtar, N., Madni, A., Shah A. S. M., Hasan, Z., Ullah, A., 2011. Amino acids: A review article. J. Med. Plants Res. 5 (17), 3997-4000.
Alaqeel, S. I., 2017. Synthetic approaches to benzimidazoles from O- phenylenediamine: A literature review, J. Saudi Chem. Soc. 21, 229-237.
Alasmary, F. A. S., Snelling, A. M., Zain, M. E., Alafeefy, A. M., Awaad, A. S., Karodiaker, N., 2015. Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents. Molecules 20, 15206-15223.
Blacker, A. J., Farah, M. M., Hall, M. I., Marsden, S. P., Saidi, O., Williams, J. M. J., 2009. Synthesis of Benzazoles by Hydrogen-Transfer Catalysis. Org. Lett. 11 (9), 2039-2042.
Cescon, L. A., Day, A. R., 1962, J. Org. Chem. 27, 581-586.
Chen, R.-H., Xiong, J.-F., Peng, P., Mo, G.-Z., Tang, X.-S., Wang, Z.-Y., Wang, X.-F., 2014. Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method. Asian J. Chem. 26 (3). 926-932.
Jun, L., Bingquin, Y., Yingjuan, B., 2002. Microwave Irradiation Synthesis of 2-substituted Benzimidazoles Using PPA as a Catalyst Under Solvent-Free Conditions. Synth. Commun. 32 (24), 139-145.
Keri, R. S., Hiremathad, A., Budagumpi, S., Nagaraja, B. M., 2014. Comprehensive Review in Current Developments of Benzimidazole – Based Medicinal Chemistry. Chem. Biol. Drug. Des. 86 (1), 19-65.
Kumar, B., Smita, K., Kumar, B., Cumbal, L., 2014. J. Chem. Sci. 126(6), 1831-1840.
Kumar, K., Awasthi, D., Lee, S.-Y., Cummings, J. E., Susan, E. K., Slayden, R. A., Ojima, I., 2013. Bioorg. Med. Chem. 21, 3318-3326.
Li, X.-N., Zhou, H.-Y., Feng, L., Duan, K., Wang, J.-X., 2012. Temperature-tuned enantioselectivity in transfer hydrogenation: preparation and catalytic property of amino acid-modified benzimidazole. Appl. Organometal. Chem. 26, 168-174.
Maekawa, K., Ohtani, J., 1976. Synthese von 2-(1’-Amino-1’-substituiertem alkyl)-benzimidazol aus Aminosuren und Ihre Biologische Aktiviät. Agr. Biol. Chem. 40, 791-799.
Nadaf, R. N., Siddiqui, S. A., Daniel, T., Lahoti, R. J., Srinivasan, K. V., 2014. Room temperature ionic liquid promoted regioselective synthesis of 2-aryl benzimidazoles, benzoxazoles and benzthiazoles under ambient conditions. J. Mol. Catal. A. Chem. 214, 155-160.
Özgür, D. C., Ümide, D. Ö., Zafer, A. K., Yusuf, Ö., 2009. Effects of Some 1,3,5-Trisubstitued-2-pyrazoline Derivatives on Depression and Anxiety Parameters of Mice. Arch. Pharm. Res. 32 (9), 1293-1299.
Padalkar, V., S., Gupta,V. D., Phatangare, K. R., Patil, V. S., Umape, P. G., Sekar, N., 2012. Indion 190 resin: efficient, environmentally friendly, and reusable catalyst for synthesis of benzimidazoles, benzoxazoles, and benzothiazoles. Green Chem. Lett. Rev. 5 (2), 139-145.
Peng, P., Xiong, J.‑F., Mo, G.‑Z. Zheng, J.‑L., Chen, R.‑H., Chen X.‑Y., Wang, Z.-Y., 2014. A concise synthesis of benzimidazoles via the microwave‑assisted one‑pot batch reaction of amino acids up to a 10‑g scale. Amino Acids 46, 2427-2433.
Phillips, M. A., 1928. CCCXVII-The Formation of 2-Substituted Benziminazoles. J. Chem. Soc. 13, 2393-2399.
Porter, Q. N., Spear, R. J., 1970. Mass Spectrometric Studies-VI: Aziridines.Org. Mass Spectrom. 3, 1259-1282.
Thakuria, H., Das, G., 2008. An expeditious one-pot solvent-free synthesis of benzimidazole derivatives. ARKIVOK 321-328.
Thompson, J. R., Ovens, J. S., Williams, V. E., Leznoff, D. B., 2013. Supramolecular Assembly of Bis(benzimidazole)pyridine: An Extended Anisotropic Ligand For Highly Birefringent Materials. Chem. Eur. J. 19, 16572-16578.
Wenker, H., 1935. The Preparation of Ethylene Imine from Monoethanolamine. J. Am. Chem. Soc. 57 (11), 2328-2328.
Publicado
2019-07-05
Cómo citar
Islas-Trejo, E., Tapia-Benavides, A. R., Suarez-Castillo, O., & Tlahuextl, M. (2019). Síntesis del 2-metil-1H-benzo[d]imidazol y 2-etil-1H-benzo[d]imidazol a partir de de L-serina, L-treonina, L-cisteína. Pädi Boletín Científico De Ciencias Básicas E Ingenierías Del ICBI, 7(13), 20-24. https://doi.org/10.29057/icbi.v7i13.3895
Tipo de manuscrito
Artículos de investigación
