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Synfacts 2010(3): 0275-0275  
DOI: 10.1055/s-0029-1219427
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Substituted Dihydropyridines from Propargyl Enol Ethers

Contributor(s): Victor Snieckus, Alcides da Silva
D. Tejedor*, G. Méndez-Abt, F. García-Tellado*
Instituto de Productos Naturales y Agrobiologia, Tenerife and Instituto Canario de Investigación del Cáncer, Las Palmas de Gran Canaria, Spain
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

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.