Please use this identifier to cite or link to this item: http://localhost:8080/xmlui/handle/123456789/2298
Title: Tandem Organocatalyzed Knoevenagel Condensation/1,3-Dipolar Cycloaddition towards highly functionalized fused 1,2,3-Triazoles
Authors: Jibi John
Joice Thomas
Nikita Parekh
Dehaen, W
Keywords: Organocatalysis ; Tandem reactions ;Cycloaddition ;Cyclization Regioselectivity ; Azides ; Nitrogen heterocycles
Issue Date: 2015
Publisher: Wiley
Citation: European Journal of Organic Chemistry (22):4922-4930,Aug 2015
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.
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