Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

The intramolecular alkyne–azide Huisgen [3+2] cycloaddition reaction as a ‘click-chemistry’ reaction without a metal catalyst has been studied under aerobic conditions. The synthesis of various pyrrolidine–triazole hybrid compounds has also been achieved by using this intramolecular cycloaddition reaction in water with complete 1,5-regioselectivity.

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((4S,5S)-5-(Azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanolC7H13N3O3[α]D25=-69.3 (c 1, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4S,5S)

(4S,5S)-4-(Azidomethyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolaneC8H11N3O2[α]D25=-109.6 (c 1, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4S,5S)

(3bS,6aS)-5,5-Dimethyl-6a,7-dihydro-3bH-[1,3]-dioxolo[4′,5′:3,4]pyrrolo[1,2-c][1,2,3]triazoleC8H11N3O2[α]D25=-64.5 (c 0.75, MeOH)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (3bS,6aS)

Methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propionateC10H13N3O4[α]D25=-98.7 (c 0.75, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4S,5S)

(3bS,6aS)-Methyl 5,5-dimethyl-6a,7-dihydro-3bH-[1,3]dioxolo[4′,5′:3,4]pyrrolo[1,2-c][1,2,3]triazole-3-carboxylateC10H13N3O4[α]D25=-86.5 (c 1, MeOH)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (3bS,6aS)

(4S,5S)-Methyl 4,5-dihydroxy-5,6-dihydro-4H-pyrrolo[1,2-c][1,2,3]triazole-3-carboxylateC7H9N3O4[α]D25=-38.5 (c 0.5, MeOH)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4S,5S)