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 tri-azole 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.
