Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides

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Smellie, Iain A. S. and Fromm, Andreas and Fabbiani, Francesca P. A. and Oswald, Iain D. H. and White, Fraser J. and Paton, R. Michael (2010) Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides. Tetrahedron, 66 (35). pp. 7155-7160. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2010.06.076)

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Abstract

Reaction of per-O-acetylated-beta-D-pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides, with 2-aminothiophenol afforded 2-(beta-D-pyranosyl)benzothiazoles. 1,2-Diaminobenzene and 2-aminophenol reacted similarly to yield 2-(beta-D-pyranosyl)benzimidazoles and 2-(beta-D-pyranosyl)benzoxazoles, respectively. The structures of 2-beta-D-glucopyranosylbenzimidazole (17), 2-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)benzimidazole (19) and the xylopyranosyl thiohydroximate 13 were established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

ORCID iDs

Smellie, Iain A. S., Fromm, Andreas, Fabbiani, Francesca P. A., Oswald, Iain D. H. ORCID logoORCID: https://orcid.org/0000-0003-4339-9392, White, Fraser J. and Paton, R. Michael;
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