Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(3): 0275-0275
DOI: 10.1055/s-0029-1219427
DOI: 10.1055/s-0029-1219427
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Substituted Dihydropyridines from Propargyl Enol Ethers
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
Further Information
Publication History
Publication Date:
18 February 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201003/lookinside/thumbnails/10.1055-s-0029-1219427-1.jpg)
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.