Revisit to the reaction of o-phenylene diamine with thiosemicarbazide to give benzimidazole-2-thione rather than benzotriazine-2-thione and its glycosylation.
Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.
El Ashry
El Sayed H
el SH
International Center for Chemical and Biological Science, H E J Research Institute of Chemistry, University of Karachi, Karachi, Pakistan. eelashry60@hotmail.com
Aly
Aly A
AA
Aouad
Mohamed R
MR
Amer
Mohammed R
MR
D001562:Benzimidazoles / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D010655:Phenylenediamines / Q000737:chemistry*; D012663:Semicarbazides / Q000737:chemistry*; D013871:Thiones / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
D001562:Benzimidazoles; D006027:Glycosides; D010655:Phenylenediamines; D012663:Semicarbazides; D013871:Thiones; D014227:Triazines; C553964:benzotriazine-2-thione; C006699:benzimidazoline-2-thione; C005151:thiosemicarbazide; C034193:1,2-diaminobenzene