N-羟基苯胺与丙炔酸酯在DMAP催化下缩合合成3-羧酸吲哚衍生物的反应。

反应机理

反应实例

To a solution of N-benzyl-N-phenylhydroxylamine1 (86.2 mg, 0.426 mmol) in THF (15.0 mL) was added 4A molecular sieves. DMAP (6.0 mg, 0.049 mmol) and methyl propiolate 2 (54 mg, 0.562 mmol) were addedto it at 0°C.  The reaction mixture was stirred at 0°C for 1 h, then at room temperature for48 h. Ethyl acetate (5.0 mL) was added, and after filtration, the organicsolution was washed with water (3 x 20 mL), brine, and then dried overmagnesium sulfate. Following filtration, the organics are concentrated underreduced pressure and the resultant oil purified by flash column chromatography(hexanes: ethyl acetate= 7:3) as eluent to give 1-benzyl-1H-indole-3-carboxylicacid methyl ester 3 (95.6 mg; 82% yield) as a white solid (m.p. 67.0-67.5°C).

Ref: (a) R.Hwu, H.V. Patel, R.J. Lin, and M.O. Gray,J. Org. Chem., 1994, 1577

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