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A Mild Protocol for the Efficient Synthesis of 5,6-Unsubstituted 1,4-Dihydropyridines

Swarupananda Maiti, J. Carlos Menéndez*

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain, Email: josecmfarm.ucm.es

S. Maiti, J. C. Menéndez, Synlett, 2009, 2249-2252.

DOI: 10.1055/s-0029-1217719 (free Supporting Information)


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Abstract

Treatment of 6-alkoxy-1,4,5,6-tetrahydropyridines with neutral alumina (activity grade I) suspended in refluxing acetonitrile, afforded 1,4-dihydropyridines in excellent yields. This method allowed an efficient synthesis of 5,6-unsubstituted dihydropyridines, which are difficult to prepare by traditional methods, from acyclic and readily available precursors.


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Key Words

eliminations, heterocycles, dihydropyridines, cerium(IV), Lewis acids


ID: J60-Y2009-2610