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Communication | Regular issue | Vol 9, No. 7, 1978, pp.841-844
Published online, 1st January, 1970
DOI: 10.3987/R-1978-07-0841
Studies on Ketene and Its Derivatives (XC). Reaction of Diketene with Ethyl Cyanoacetate and Malononitrile

Tetsuzo Kato,* Yukio Kubota, Michiko Tanaka (née Ishikawa), Hitoshi Takahashi, and Takuo Chiba

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Reaction of diketene with ethyl cyanoacetate (7) gives ethyl 2-amino-6-methyl-4-pyrone-3-carboxylate (9), which is transformed to ethyl 4-hydroxy-6-methyl-2-pyridone-3-carboxylate (11). Similarly, diketene reacts with malononitrile (8) to give 2-amino-3-cyano-6-methyl-4-pyrone (10), which is converted to 3-cyano-4-hydroxy- 6-methyl-2-pyridone (12).