Intercepted-Knoevenagel condensation for the synthesis of unsymmetrical fused-tricyclic 4H-pyrans |
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Authors: | Charles Shearer Oriane Desaunay Stephen Zorc Alexis D. Richaud Shyam S. Samanta Nagalakshmi Jeedimalla Stéphane P. Roche |
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Affiliation: | Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431, United States |
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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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Keywords: | Corresponding author. Intercepted-Knoevenagel condensation Multicomponent reaction Domino reaction Hydrogen-bond network |
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