Synthesis and Crystal Structures of Benzimidazole-2-thione Derivatives by Alkylation Reactions

El Sayed H El Ashry; Yeldez El Kilany; Nariman M Nahas; Assem Barakat; Nadia Al-Qurashi; Hazem A Ghabbour; Hoong-Kun Fun

doi:10.3390/molecules21010012

Synthesis and Crystal Structures of Benzimidazole-2-thione Derivatives by Alkylation Reactions

Molecules. 2015 Dec 22;21(1):E12. doi: 10.3390/molecules21010012.

Authors

El Sayed H El Ashry¹, Yeldez El Kilany^{2

3}, Nariman M Nahas⁴, Assem Barakat^{5

6}, Nadia Al-Qurashi⁷, Hazem A Ghabbour⁸, Hoong-Kun Fun⁹

Affiliations

¹ Chemistry Department, Faculty of Science, Alexandria University, P. O. Box 426, Alexandria 21321, Egypt. eelashry60@hotmail.com.
² Chemistry Department, Faculty of Science, Alexandria University, P. O. Box 426, Alexandria 21321, Egypt. yeldez244@hotmail.com.
³ Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah 21955, Saudi Arabia. yeldez244@hotmail.com.
⁴ Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah 21955, Saudi Arabia. narinahas@hotmail.com.
⁵ Chemistry Department, Faculty of Science, Alexandria University, P. O. Box 426, Alexandria 21321, Egypt. ambarakat@ksu.edu.sa.
⁶ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. ambarakat@ksu.edu.sa.
⁷ Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah 21955, Saudi Arabia. maam10@hotmail.com.
⁸ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.
⁹ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. hfun.c@ksu.edu.sa.

Abstract

Alkylated, benzylated and bromoalkylated benzimidazole-thione that intramolecularly heterocyclized to 3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazole were synthesized. The chemical structure of the synthesized product was characterized by Infra Red, ¹H-NMR, (13)C-NMR, and Mass spectroscopy. Furthermore, the molecular structures of 8 and 9 were confirmed by X-ray single crystallography in different space groups, Pbca and P2₁/c, respectively.

Keywords: X-ray; benzimidazole-thione; thiazino[3,2-a]benzimidazole.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Benzimidazoles / chemical synthesis
Benzimidazoles / chemistry*
Crystallography, X-Ray
Hydrogen Bonding
Models, Molecular
Molecular Structure
Sulfhydryl Compounds / chemical synthesis
Sulfhydryl Compounds / chemistry*

Substances

Benzimidazoles
Sulfhydryl Compounds