Abstract
Facile synthesis of fused 1,2,3-triazoles by a proline-catalyzed reaction of an azido aldehyde and a nitroalkane is elaborated. The present tandem protocol proceeds via an organocatalytic Knoevenagel condensation of the azido aldehyde and nitroalkane followed by intramolecular azide–nitroalkene cycloaddition. The functionalized bicyclic triazole is obtained by elimination of HNO2 from the cycloadduct. Application of this strategy enabled us to synthesize a range of functionalised 5–7 membered ring fused triazoles. The reaction calls for mild conditions, affords high yields, and results in good regiospecificity while displaying excellent substrate scope.
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