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Condensation of 2-amino-2-deoxysugars with isothiocyanates. Synthesis ofcis-1,2-fused glycopyrano heterocycles.

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
50
Issue
10
Identifiers
DOI: 10.1016/s0040-4020(01)81122-4

Abstract

Abstract The reactions of 2-amino- and 2-alkylamino-2-deoxyglycopyranoses with isothiocyanates gave thioureas and heterocyclic derivatives. Moreover, cis-fused glycopyrano[2,1- d]imidazolidin-2-thiones, which have a close structural analogy with some naturally-occurring glycosidase inhibitors, were synthesised for the first time. The mechanism of formation of glycofurano and glycopyrano[2,1- d]imidazolidin-2-thiones occurs via the intermediacy of monocyclic 5-hydroxyimidazolidin-2-thiones. These substances are generated by intramolecular nucleophilic addition of an NH group to the aldehyde function of the sugar. The monocyclic intermediates have been isolated and their participation in the formation of bicyclic imidazolidin-2-thiones and/or monocyclic imidazolin-2-thiones proved. In stark contrast, cis-fused glycopyranothiazolidines were prepared by nucleophilic displacements.

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