１，４‐位に置換基をもつアントラキノンの還元

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タイトル別名
  • Reductions of Anthraquinones Having Substituents at 1, 4-Positions with Various Reducing Reagents

説明

Anthraquinones which have the hydroxyl, acetoxyl, methoxyl and amino groups at 1, 4-positions were reduced by granulated tin-hydrochloric acid (method A), tin (II) chloridehydrochloric acid (method B), zinc dust-hydrocholoric acid (method C), lithium aluminum hydride in THF (method D), sodium borohydride in methanol (method E) and sodium dithionite-sodium hydroxide (method F) under standard conditions. Reduction of 1, 4dihydroxyanthraquinone (quinizarin) with the method A, B, or C gave 9, 10-dihydroxy-1, 2, 3, 4-tetrahydro-1, 4-anthracenedione(leucoquinizarin), and reduction with the method D, E, or F gave 1, 4-anthracenedione. Reduction of 1, 4-diacetoxyanthraquinone with the method A, B, C, or F yielded leucoquinizarin, and the method D or E gave 1, 4-anthracenedione.1, 4-Dimethoxyanthraquinone gave leucoquinizarin by reduction with the method A, B, or C, but reduction with the method D, E, or F yielded 9, 10-dihydro-1, 4-dimethoxy-9, 10anthracenediol, 1, 4-dimethoxyanthrone, and 1, 4-dimethoxyanthracene. Reduction of 1amino-4-hydroxyanthraquinone with the method A or B gave leucoquinizarin with a small amount of quinizarin, and the method C and E gave 9, 10-dihydroxy-1, 2, 3, 4-tetrahydro-1anthracenone, respectively. The method D yeilded 1-amino-4-hydroxyanthrone. Leucoquinizarin was obtained by the reduction of 1, 4-diaminoanthraquinone with the method A, B, or F but method C and E yielded 9, 10-dihydroxy-1, 2, 3, 4-tetrahydro-1-anthracenone and 1, 2, 3, 4-tetrahydroanthraquinone, respectively. In the case of reductions of 1, 2, 4-trihydroxyanthraquinone(purpurin), the method A, B and F eliminated one of the hydroxyl groups and gave both leucoquinizarin and 1, 3-dihydroxyanthrone, and the method C and E yielded 1, 4-anthracenedione along with leucoquinizarin. Reduction of 1, 2, 5, 8-tetrahydroxyanthraquinone(quinalizarin) with the method A, B, or F gave leuco derivative of quinalizarin, and the method D and F gave 5, 6-dihydroxy-1, 4-anthraquinone.

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