Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition ‘click-chemistry’ in water

The synthesis of a new class of hybrid 1,2,3-triazozlo-δ-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition ‘click-chemistry’ reaction of various organic azides with an activated alkyne in water, followed by cyclization.

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(S)-Methyl 6-(hydroxymethyl)-4-oxo-6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]oxazine-3-carboxylateC8H9N3O5[α]D20=+5.72 (c 0.75, CHCl3)Source of chirality: (R)-glyceraldehydeAbsolute configuration: (S)

(S)-Dimethyl 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylateC12H17N3O6[α]D20=+11.19 (c 1, CHCl3)Source of chirality: (R)-glyceraldehydeAbsolute configuration: (S)

Dimethyl 1-(((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylateC13H19N3O7[α]D20=-34.55 (c 1, CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: (4S,5S)

Tetramethyl 1,1′-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)bis(1H-1,2,3-triazole-4,5-dicarboxylate)C19H24N6O10[α]D20=-46.9 (c 0.5, CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: (4S,5S)