Intercepted-Knoevenagel condensation for the synthesis of unsymmetrical fused-tricyclic 4 H -pyrans.
Tetrahedron(2019)
Abstract
4H-Pyrans (4H-Pys) and 1,4-dihydropyridines (1,4-DHPs) are important classes of heterocyclic scaffolds in medicinal chemistry. Herein, an indium(III)-catalyzed one-pot domino reaction for the synthesis of highly functionalized 4H-Pys, and a model of 1,4-DHP is reported. This alternative approach to the challenging Hantzsch 4-component reaction enables the synthesis of fused-tricyclic heterocycles, and the mechanistic studies underline the importance of an intercepted-Knoevenagel adduct to achieve higher chemoselectivity towards these types of unsymmetrical heterocycles.
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Key words
Intercepted-Knoevenagel condensation,Multicomponent reaction,4H-pyrans,Domino reaction,Hydrogen-bond network
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