TY - JOUR
T1 - Synthesis and structure of sulfur derivatives from 2-aminobenzimidazole
AU - Cruz, Alejandro
AU - Padilla-Martínez, Itzia I.
AU - García-Báez, Efrén V.
AU - Guerrero-Muñoz, Gerardo
N1 - Publisher Copyright:
© 2014 by the authors; licensee MDPI, Basel, Switzerland.
PY - 2014/9/4
Y1 - 2014/9/4
N2 - 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 dimethyldithiocarboimidate 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.
AB - 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 dimethyldithiocarboimidate 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.
KW - 2-aminobenzimidazole
KW - Dithio-methylcarboimidates
KW - Dithiocarbamates
KW - S-methyldithiocarbamates
UR - http://www.scopus.com/inward/record.url?scp=84908177587&partnerID=8YFLogxK
U2 - 10.3390/molecules190913878
DO - 10.3390/molecules190913878
M3 - Artículo
C2 - 25255762
AN - SCOPUS:84908177587
SN - 1420-3049
VL - 19
SP - 13878
EP - 13893
JO - Molecules
JF - Molecules
IS - 9
ER -