Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Sulfinylamine Chemistry. I. A New Degradation Reaction of α-Amino Acid with N-Sulfinylaniline
田口 胤三森田 士郎川副 裕一
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1975 年 23 巻 11 号 p. 2654-2659

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Analogously to the Strecker degradation method, α-amino acids were converted to carbonyl derivatives by treatment with N-sulfinylaniline below 100° in dimethylsulfoxide (or benzene). The sodium salts prefer to the free acids as substrates (35-75% yield). In contrast with other α-amino acids, glycine was further oxidized to formic acid derivative. Also, α-amino acid ethyl esters were submitted to the same treatment and usually converted to keto acid esters as expected. However, the reaction of ethyl glycinate proceeded unordinarily to afford diethyl 1, 2, 5-thiadiazole-3, 4-dicarboxylate. The degradation reaction pathway of α-amino acids was discussed with some evidences and speculations.
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© The Pharmaceutical Society of Japan
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