Synthesis of 2-methyl-1H-benzo [d] imidazole and 2-ethyl-1H-benzo [d] imidazole from L-serine, L-threonine, L-cysteine.
Keywords:
2-methylbenzimidazole, 2-ethylbenzimidazole, α-aminoacids, o-phenylenediamine, microwave, NMR
Abstract
2-Methyl-1H-benzo[d]imidazole (5) and 2-ethyl-1H-benzo[d]imidazole (6) were obtained by the reaction of o-phenylenediamine with L-serine, L-cysteine or L- threonine respectively. The induction of the reaction was carried out by using two alternative methodologies: Fusion or Microwave Radiation (MW). The use of these synthetic processes turned out to be simple and efficient. However, it is essential to use the appropriate equipment to carry out these chemical reactions. The molecular structure of 5 and 6 was determined by 1H, 13C NMR and X-ray diffraction. The probable reaction mechanism proposed in the present work involves the loss of water, hydrogen cyanide and migration of hydrogen atoms (or of the methyl group).
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References
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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.
Published
2019-07-05
How to Cite
Islas-Trejo, E., Tapia-Benavides, A. R., Suarez-Castillo, O., & Tlahuextl, M. (2019). Synthesis of 2-methyl-1H-benzo [d] imidazole and 2-ethyl-1H-benzo [d] imidazole from L-serine, L-threonine, L-cysteine. Pädi Boletín Científico De Ciencias Básicas E Ingenierías Del ICBI, 7(13), 20-24. https://doi.org/10.29057/icbi.v7i13.3895
Section
Research papers
