Pyrrolo[1,2-α]indole誘導体の合成
1974 年 94 巻 2 号 p. 181-188
詳細
1974 年 94 巻 2 号 p. 181-188
By treatment with acetic anhydride and acetic acid, 1-(2-carboxyphenyl)-3, 4-dimethylpyrroles (1) gave 1, 2-dimethyl-9H-pyrrolo[1, 2-α]indol-9-ones (2) in a good yield. 3-Cyano derivatives (4) were synthesized by bromination of 2 with bromine or N-bromosuccinimide to 3-bromo derivatives (3) followed by treatment of the latter with cuprous cyanide. Hydrolysis of 4 gave 1, 2-dimethyl-9-oxo-9H-pyrrolo[1, 2-α]indole-3-carboxylic acids (5) and the rearranged products, whose structure was assumed as 8, 9-dimethyl-7-hydroxy-6, 10-dihydropyrido[1, 2-α]indole-6, 10-diones (6) on the basis of the spectroscopic properties. The ratio of the products 5/6 varied with the position of chloro group on the phenyl ring. Hydrolysis of 3 with aqueous potassium hydroxide yielded 1, 2-dimethyl-9-hydroxy-3H-pyrrolo[1, 2-α]indol-3-ones (11). The same product 11e was also obtained by oxidation of 2e with lead tetraacetate.
