Cyclic Tautomers of Tryptophans and Tryptamines. VIII. Cyclic Tautomers of cyclo-L-Prolyl-L-tryptophyl and Related Compounds

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概要

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• Two diastereomers (6 and 7) of the cyclic tautomer of cyclo-L-propyl-L-tryptophyl (5) have been prepared by dissolving 5 in 85% phosphoric acid or trifluoroacetic acid. The stable isomer (6) was obtained in 89% yield on the acid treatment of 5 at room temperature. Cyclic tautomers (15 and 17) of the related 2,5-piperazinediones (14 and 16) have also been prepared. Hydroxylation of the N-acetyl cyclic tautomers (8 and 9) with lead tetraacetate in trifluoroacetic acid followed by methylation gave the 8- and 9-methoxy derivatives (18,19,21,and 22) in moderate yields. The 9-methoxy derivative (22) was the major product of the oxidation of 9. On the other hand, oxidation of 5 in trifluoroacetic acid with lead tetraacetate followed by reduction with zinc gave the 8-hydroxy derivative (28) selectively in good yield via the cyclic tautomer (26) and the quinoneimine (27).

• 社団法人日本薬学会の論文
• 1985-11-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 谷口 幹雄

  Faculty of Pharmaceutical Sciences, Chiba University

• 山本 一郎

  Faculty of Pharmaceutical Sciences, Chiba University

• 谷口 幹雄

  Faculty Of Pharmaceutical Sciences Chiba University

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 山本 一郎

  Faculty Of Pharmaceutical Sciences Chiba University

• 中川 昌子

  千葉大 薬

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