Synthesis and Structure of Sulfur Derivatives from 2-Aminobenzimidazole

The reactions of the benzimidazole nitrogen atoms and the exocyclic amino group of 2-aminobenzimidazole with CS2 in NaOH basic medium followed by methylation with methyl iodide was explored. With careful control of the stoichiometric quantities and addition sequences, this set of reactions allows t...

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Bibliographic Details
Main Authors: Alejandro Cruz, Itzia I. Padilla-Martínez, Efrén V. García-Báez, Gerardo Guerrero-Muñoz
Format: Article
Language:English
Published: MDPI AG 2014-09-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/19/9/13878
Description
Summary:The reactions of the benzimidazole nitrogen atoms and the exocyclic amino group of 2-aminobenzimidazole with CS2 in NaOH basic medium followed by methylation with methyl iodide was explored. With careful control of the stoichiometric quantities and addition sequences, this set of reactions allows the selective functionalization of the benzimidazole ring with N-dithiocarbamate, S-methyldithiocarbamate or dimethyl- dithiocarboimidate groups. The products were characterized by 1H-, 13C-NMR spectroscopy and three of them by X-ray diffraction analysis. The preferred isomers, tautomers and conformers were established.
ISSN:1420-3049