Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method

Ren-Hong Chen; Jin-Feng Xiong; Pai Peng; Guang-Zhen Mo; Xing-San Tang; Zhao-Yang Wang; Xiu-Fang Wang

doi:10.14233/ajchem.2014.16438

Issue

Vol. 26 No. 3 (2014): Vol 26 Issue 3

Issue Published : January 30, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method

https://doi.org/10.14233/ajchem.2014.16438

Ren-Hong Chen

Guangdong Food and Drug Vocational College, LongDong North Road, TianHe Restrict, Guangzhou 510520, P.R. China

Jin-Feng Xiong

School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P.R. China

Pai Peng

School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P.R. China

Guang-Zhen Mo

School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P.R. China

Xing-San Tang

Guangdong Food and Drug Vocational College, LongDong North Road, TianHe Restrict, Guangzhou 510520, P.R. China

Zhao-Yang Wang

School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P.R. China

Xiu-Fang Wang

College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, P.R. China

Corresponding Author(s) : Ren-Hong Chen

chenrenhong306@163.com

Asian Journal of Chemistry, Vol. 26 No. 3 (2014): Vol 26 Issue 3
Article Published : January 31, 2014

Abstract

By using low cost and readily available amino acids as the synthetic blocks, a series of 2-aminomethyl-benzimidazole are synthesized with solvent-free melting method. While the condensation of aspartic acid (or asparagine) with o-diaminobenzene gives the fluorescent bisbenzimidazole product without amino group via the further deamination reaction in the melting reaction system. The condensation reactions between most amino acids and o-diaminobenzenes exhibits higher yields of 58 to 86 % (mostly over 66 %), shorter reaction time (5 h) than that previously reported and better tolerance for different functional groups in amino acids. The structures of twenty benzimidazoles with multifunctional groups, including thirteen new compounds, are systematically characterized with FTIR, ¹H NMR, ¹³C NMR, MS and elemental analysis. These investigations are beneficial to the further researches on their applications in biochemistry, coordination chemistry and organic synthesis intermediates.

Keywords

Benzimidazole Synthesis Amino acid Solvent-free melting method Condensation

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 Journal of Chemistry, 26(3), 926–932. https://doi.org/10.14233/ajchem.2014.16438

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References

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Y. Liu, A. Kumar, S. Depauw, R. Nhili, M.H. David-Cordonnier, M.P. Lee, M.A. Ismail, A.A. Farahat, M. Say, S. Chackal-Catoen, A. Batista-Parra, S. Neidle, D.W. Boykin and W.D. Wilson, J. Am. Chem. Soc., 133, 10171 (2011); doi:10.1021/ja202006u.

Y. Bansal and O. Silakari, Bioorg. Med. Chem., 20, 6208 (2012); doi:10.1016/j.bmc.2012.09.013.

B. Narasimhan, D. Sharma and P. Kumar, Med. Chem. Res., 21, 269 (2012);doi:10.1007/s00044-010-9533-9.

Z.Z. Mao, Z.Y. Wang, X.N. Hou, X.M. Song and Y.F. Luo, Chin. J. Org. Chem., 28, 542 (2008).

Z.Z. Mao, Z.Y. Wang, W.J. Mei and K. Yang, Chin. J. Chem., 28, 818 (2010); doi:10.1002/cjoc.201090152.

S.P. Velagapudi, S.J. Seedhouse, J. French and M.D. Disney, J. Am. Chem. Soc., 133, 10111 (2011); doi:10.1021/ja200212b.

F. Bischoff, D. Berthelot, M. De Cleyn, G. Macdonald, G. Minne, D. Oehlrich, S. Pieters, M. Surkyn, A.A. Trabanco, G. Tresadern, S. Van Brandt, I. Velter, M. Zaja, H. Borghys, C. Masungi, M. Mercken and H.J.M. Gijsen, J. Med. Chem., 55, 9089 (2012); doi:10.1021/jm201710f.

Z.Z. Mao, Z.Y. Wang, J.N. Li, X.M. Song and Y.F. Luo, Synth. Commun., 40, 1963 (2010); doi:10.1080/00397910903219328.

T.B. Nguyen, L. Ermolenko and A. Al-Mourabit, J. Am. Chem. Soc., 135, 118 (2013); doi:10.1021/ja311780a.

M. Ghate, P. Devi, J. Parikh and V.K. Vyas, Med. Chem., 9, 474 (2013); doi:10.2174/1573406411309030017.

S.F. Zhou, F.B. Li, P.Z. Zhang and L. Jiang, Res. Chem. Intermed., 39, 1735 (2013); doi:10.1007/s11164-012-0708-5.

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J.G. Wilson and F.C. Hunt, Aust. J. Chem., 36, 2317 (1983); doi:10.1071/CH9832317.

K.R. Reddy, G.G. Krishna and C.V. Rajasekhar, Synth. Commun., 37, 4289 (2007); doi:10.1080/00397910701575335.

K. Maekawa and J. Ohtani, Agric. Biol. Chem., 40, 791 (1976); doi:10.1271/bbb1961.40.791.

D. Max and S. Adolf-Emil, Switz. Patent 430728 (1967).

K.C. Tsou, D.J. Rabiger and B. Sobel, J. Med. Chem., 12, 818 (1969); doi:10.1021/jm00305a022.

D.D. Rishipathak, S.C. Pal, S.C. Mandal and D.P. Belsarea, Asian J. Chem., 19, 3242 (2007).

N. Perìn, L. Uzelac, I. Piantanida, G. Karminski-Zamola, M. Kralj and M. Hranjec, Bioorg. Med. Chem., 19, 6329 (2011); doi:10.1016/j.bmc.2011.09.002.

Issue

Vol. 26 No. 3 (2014): Vol 26 Issue 3

Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method

Corresponding Author(s) : Ren-Hong Chen

Abstract

Keywords

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