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

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;
CORE (COnnecting REpositories)