Abstract
The first synthesis of unsaturated halogeno-ketonucleosides has been accomplished by oxidation of 3′,4′-anhydrohexosylpurines followed by the action of lithium halide on the keto-anhydro-intermediate. Nucleophilic additions to these new compounds were especially studied. Sodium borohydride was shown to add to the carbonyl group providing a new and simple route to unsaturated nucleosides. Hydrazoic acid added to the double bond by a 1,2-addition mechanism, leading to a triazolo-nucleoside. 1,4-Addition of cyclohexylamine followed by intra molecular elimination of bromine afforded an epimino-nucleoside, which constituted the first example of an aziridine derivative in the nucleoside field. The structure of the new compounds obtained was ascertained from a study of their 1H and 13C n.m.r. spectra.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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