Reactions of Acyl-aminoquinone Tosylhydrazones. I. A New Synthesis of Pyrrolo [1,2-α] indoloquinones and Related Compounds
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Novel synthesis of pyrrolo [1,2-α] indoloquinones, indazoloquinones, and related compounds, which seem to possess the same biological activities as those of mitomycins and rifamycin derivatives, are reported. 2-Acetyl-5-methylhydroquinone tosylhydrazone was oxidized with potassium nitrosodisulfonate affording 2-acetyl-5-methyl-1,4-benzoquinone tosylhydrazone (9). On treatment with amines (pyrrolidine (a), piperidine (b), morpholine (c), and diethylamine (d)), 9 gave 2-acetyl-3-amino-5-methyl-1,4-benzoquinone tosylhydrazones (10a-d). 2,3-Dihydro-6,9-dimethyl-5,8-dioxo-1H-pyrrolo [1,2-α] indole and the analogous products (14a-d) were obtained by heating 10a-d at their melting points without a solvent. Along with 14a-d, ditolyl disulfide, ditolyl thiolsulfonate and 4,7-dihydroxy-3,6-dimethyl-1-tosyl-1H-indazole (16) were obtained as minor products in all these cases.
- 公益社団法人日本薬学会の論文
- 1977-02-25
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