Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Diels-Alder Reaction of 4-Carboxymethyl-5-ethoxyoxazole
TAISUKE MATSUOTAKUICHI MIKI
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1972 Volume 20 Issue 4 Pages 806-814

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Abstract
The Diels-Alder reaction of 4-carboxymethyl-5-ethoxyoxazole (I) was investigated. First, the mechanism and the stereochemistry of the adducts in the course of the Diels-Alder reaction were discussed. Second, the reaction of I with asymmetrical dienophiles gave the substance that an electron attracting group was preferentially introduced at γ-position of pyridine nucleus. Finally, the reaction of I with maleic anhydride, fumaric acid, maleic acid and methacrylic acid afforded the decarboxylated compounds. The mechanism of these reaction was discussed.
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© The Pharmaceutical Society of Japan
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