Oxidative free radical reactions between 2-amino-1,4-benzoquinones and carbonyl compounds |
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Authors: | Che-Ping Chuang An-I Tsai |
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Institution: | Department of Chemistry, National Cheng Kung University, Tainan 70101, Taiwan, ROC |
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Abstract: | The manganese(III) initiated oxidative free radical reactions of 2-amino-1,4-benzoquinone are described. The free radical reaction of 5,6-dimethyl-2-methylamino-1,4-benzoquinone (1) provides a novel method for the synthesis of indole-4,7-dione and indole-2,4,7-trione. High chemoselectivity was observed in different solvents. The regioselectivity of this reaction was also studied with 5-methyl-2-methylamino-1,4-benzoquinone (19). In most cases, indole-4,7-diones 20 and 21 were produced in high regioselectivity. |
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Keywords: | Manganese(III) acetate Free radical 2-Amino-1 4-benzoquinones Solvent effects Regioselectivity |
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