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Revisit to the Reaction of O-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation
Journal article   Peer reviewed

Revisit to the Reaction of O-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation

El Sayed H. El Ashry, Aly A. Aly, Mohamed R. Aouad and Mohammed R. Amer
Nucleosides, nucleotides & nucleic acids, Vol.29(9), pp.698-706
09/2010
PMID: 20706960

Abstract

Biochemistry & Molecular Biology Life Sciences & Biomedicine Science & Technology
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.

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