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Tandem Organocatalyzed Knoevenagel Condensation/1,3‐Dipolar Cycloaddition towards Highly Functionalized Fused 1,2,3‐Triazoles
Author(s) -
John Jubi,
Thomas Joice,
Parekh Nikita,
Dehaen Wim
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500459
Subject(s) - knoevenagel condensation , chemistry , cycloaddition , aldehyde , intramolecular force , combinatorial chemistry , nitroalkene , organocatalysis , tandem , azide , organic chemistry , click chemistry , catalysis , enantioselective synthesis , materials science , composite material
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 HNO 2 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.