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 International Center for Chemical and Biological Science, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan; Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt

Aly A. Aly Chemistry Department, Faculty of Science, Benha University, Benha, Egypt

Mohamed R. Aouad Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt; Chemistry Department, Faculty of Science, University of Science and Technology, Oran, Oran, Algeria

Mohammed R. Amer International Center for Chemical and Biological Science, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan

Abstract

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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Acknowledgments

The authors thank the Higher Education Commission (H. E. C.) Pakistan for their valuable support (Project No. 20-697/R&D/06/38). Thanks also are due to Prof. Dr. Atta-Ur-Rahman and Prof. Dr. M. I. Choudhary for their valuable help.

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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

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