Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes

Abstract

Highly functionalized regio-and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic -lactam 7 or -lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

“…1) [8–9]. The 1,2,3-triazole moiety is a constituent part of many modified nucleosides or carbanucleosides with antiviral, anti-HIV or cytostatic activities [10–12]. However, the scope of triazole chemistry is not confined to drug discovery.…”