Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Syntheses of 2 (1H)-Pyridone Derivatives. II. Reactions of N-Substituted 6-Chloro-2 (1H)-pyridones with Ethylenediamine, 2-Aminoethanethiol and Related Compounds
久保 一夫伊藤 徳樹磯村 八州男僧都 勲本間 弘茂村上 増雄
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キーワード: analgesic activity
ジャーナル フリー

1979 年 27 巻 5 号 p. 1207-1213

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It has been found that Smiles rearrangement leading to N-p-chlorophenyl-6-β-hydroxyethylamino-4-phenyl-2 (1H)-pyridone (II) took place when 6-β-aminoethoxy-N-p-chlorophenyl-4-phenyl-2 (1H)-pyridone (III) was heated in acetic acid, and that the reaction of an N-substituted 6-chloro-4-phenyl-2 (1H)-pyridone (I) with ethylenediamine, 2-amino-ethanethiol or o-aminothiophenol gives condensed heterocyclic pyridones such as imidazopyridone (IV), thiazolopyridone (X) or benzothiazolopyridone (XV). This reaction is considered to proceed by ring transformation of an intermediate of the Smiles rearrangement. Some of these pyridone derivatives showed strong biological activities as analgesic and antiinflammatory agents.
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© The Pharmaceutical Society of Japan
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