Abstract
Reported is a synthesis of substituted alkyl 1,2-dihydropyridine-3-carboxylates by microwave-assisted Claisen rearrangement-isomerization-amine condensation-6π-aza-cascade reaction of propargyl enol ethers with primary amines. For these domino reactions, the application of MW irradiation (150 W, 120 ˚C, 30 min, toluene) gave the best yields. The reaction proceeded for a broad spectrum of amines although aromatic amines gave better yields than aliphatic amines. A modest diastereoinduction (50% de) was observed when a chiral amine was used. The procedure was applied to prepare nicotinic acid derivatives, by using MeONH2˙HCl instead of primary amines.
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