A new synthesis of N-alkyl 4-methyl-1,4-dihydropyridines utilizing sec-aminodienyl esters with crotonaldehyde.
The reactions of sec-aminodienyl esters 3 with crotonaldehyde (4) afforded N-alkyl 3-[2-(methoxycarbonyl)ethenyl]-4-methyl-1,4-dihydropyridines 5, providing a new azaelectrocyclization reaction.
Koike
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Showa Pharmaceutical University, Machida, Tokyo, Japan. koike@ac.shoyaku.ac.jp
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D000447:Aldehydes; D000475:Alkenes; D004952:Esters; D011725:Pyridines; C012796:2-butenal