Improved Method of S-Alkylation of 2-Mercaptobenzimidazole Derivatives with Trialkylphosphite

A. El-Kihel; S. Zouitina; S. Guesmi; M. Ahbala; P. Bauchat; B. Biersack

doi:10.14233/ajchem.2016.19647

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

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

Improved Method of S-Alkylation of 2-Mercaptobenzimidazole Derivatives with Trialkylphosphite

https://doi.org/10.14233/ajchem.2016.19647

A. El-Kihel

Laboratoire de Chimie Bioorganique, Faculté des Sciences, BP20, 24000, El Jadida, Morocco

S. Zouitina

Laboratoire de Chimie Bioorganique, Faculté des Sciences, BP20, 24000, El Jadida, Morocco; Laboratoire de Chimie de Coordination et d'Analytique, Faculté des Sciences, BP20, 24000, El Jadida, Morocco

S. Guesmi

Laboratoire de Chimie de Coordination et d'Analytique, Faculté des Sciences, BP20, 24000, El Jadida, Morocco

M. Ahbala

Laboratoire de Chimie Bioorganique, Faculté des Sciences, BP20, 24000, El Jadida, Morocco

P. Bauchat

Université de Rennes1, Sciences Chimiques de Rennes U.M.R. 6226, ICMV, Campus de Beaulieu, Avenue Général Leclerc, 35042, Rennes, France

B. Biersack

Organic Chemistry Laboratory, University of Bayreuth, Universitaetsstrasse 30, NW 1, 95447 Bayreuth, Germany

Corresponding Author(s) : A. El-Kihel

abdellatifelkihel@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

A new method of S-alkylation of 2-mercaptobenzimidazole derivatives has been developed by the condensation of these heterocycles with trialkylphosphite in the presence of phosphorus oxychloride giving the corresponding 2-S-alkylbenzimidazoles. The structure of the obtained products has been established by spectroscopic data.

Keywords

2-Mercaptobenzimidazole 2-S-alkylbenzimidazoles Trialkylphosphite Phosphorus oxychloride S-alkylation

El-Kihel, A., Zouitina, S., Guesmi, S., Ahbala, M., Bauchat, P., & Biersack, B. (2016). Improved Method of S-Alkylation of 2-Mercaptobenzimidazole Derivatives with Trialkylphosphite. Asian Journal of Chemistry, 28(6), 1267–1269. https://doi.org/10.14233/ajchem.2016.19647

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References

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A. El Kihel, M. Ahbala, A. Mouzdahir, N. Snader, E. Mokhtar Essassi, P. Bauchat and R. Danion-Bougot, Synth. Commun., 38, 200 (2008); doi:10.1080/00397910701738933.
A.E. Kihel, M. Benchidmi, E.M. Essassi, P. Bauchat and R. Danion-bougot, Synth. Commun., 29, 2435 (1999); doi:10.1080/00397919908086250.
A.E. Kihel, M. Benchidmi, E.M. Essassi and R. Danion-Bougot, Synth. Commun., 29, 387 (1999); doi:10.1080/00397919908085780.
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References

H. Firouzabadi and A. Jamalian, J. Sulfur Chem., 29, 53 (2008); doi:10.1080/17415990701684776.

R.J. Cremlyn, Introduction to Organo-Sulfur Chemistry, Wiley & Sons, New York (1996).

M.D. McReynolds, J.M. Dougherty and P.R. Hanson, Chem. Rev., 104, 2239 (2004); doi:10.1021/cr020109k.

J.Y. Hwang and Y.-D. Gong, J. Comb. Chem., 8, 297 (2006); doi:10.1021/cc050149c.

G. Solladie, Synthesis, 185 (1981); doi:10.1055/s-1981-29378.

L.Y. Goh, M.E. Teo, S.B. Khoo, W.K. Leong and J.J. Vittal, J. Organomet. Chem., 664, 161 (2002); doi:10.1016/S0022-328X(02)01977-0.

C.A. Christensen and M. Meldal, J. Comb. Chem., 9, 79 (2007); doi:10.1021/cc0600627.

A.S. Abd El-All, A.A. Magd-El-Din, S.A. Osman, H.A. Yosef and T.S. Hafez, Australian J. Basic Appl. Sci., 5, 1335 (2011).

M.M. Sidky, M.R. Mahran, M.F. Zayed, W.M. Abdou and T.S. Hafez, Org. Prep. Proced. Int., 14, 225 (1982); doi:10.1080/00304948209354916.

P. Brownbridge and I. C. Jowett, Phosphorus, Sulfur, 35, 311 (1988); doi:10.1080/03086648808074335.

M. Takahashi, T. Gunji and A. Ichikawa, J. Heterocycl. Chem., 39, 1029 (2002); doi:10.1002/jhet.5570390527.

A. El Kihel, M. Ahbala, A. Mouzdahir, N. Snader, E. Mokhtar Essassi, P. Bauchat and R. Danion-Bougot, Synth. Commun., 38, 200 (2008); doi:10.1080/00397910701738933.

A.E. Kihel, M. Benchidmi, E.M. Essassi, P. Bauchat and R. Danion-bougot, Synth. Commun., 29, 2435 (1999); doi:10.1080/00397919908086250.

A.E. Kihel, M. Benchidmi, E.M. Essassi and R. Danion-Bougot, Synth. Commun., 29, 387 (1999); doi:10.1080/00397919908085780.

A.V. Raghu, G.S. Gadaginamath and T.M. Aminabhavi, J. Appl. Polym. Sci., 98, 2236 (2005); doi:10.1002/app.22434.

A.V. Raghu, G.S. Gadaginamath, N.N. Mallikarjuna and T.M. Aminabhavi, J. Appl. Polym. Sci., 100, 576 (2006); doi:10.1002/app.23334.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Improved Method of S-Alkylation of 2-Mercaptobenzimidazole Derivatives with Trialkylphosphite

Corresponding Author(s) : A. El-Kihel

Abstract

Keywords

Full Article

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