Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides |
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| Authors: | Iain AS Smellie |
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| Institution: | School of Chemistry, The University of Edinburgh, The King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK |
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| Abstract: | Reaction of per-O-acetylated-β-d-pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides, with 2-aminothiophenol afforded 2-(β-d-pyranosyl)benzothiazoles. 1,2-Diaminobenzene and 2-aminophenol reacted similarly to yield 2-(β-d-pyranosyl)benzimidazoles and 2-(β-d-pyranosyl)benzoxazoles, respectively. The structures of 2-β-d-glucopyranosylbenzimidazole (17), 2-(2,3,4-tri-O-acetyl-β-d-xylopyranosyl)benzimidazole (19) and the xylopyranosyl thiohydroximate 13 were established by X-ray crystallography. |
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| Keywords: | Nitrile oxides C-Glycosides Pyranosyl benzimidazoles Pyranosyl benzoxazoles Pyranosyl benzothiazoles X-ray crystallography |
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