Improvements in or relating to indole derivatives
The invention comprises indole-aldehydes of the formula where R is aralkoxy, and their preparation from the corresponding R-substituted indoles by reaction with an N : N-disubstituted formamide in the presence of a condensing agent and alkaline hydrolysis of the product. The aldehydes can be conden...
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Zusammenfassung: | The invention comprises indole-aldehydes of the formula where R is aralkoxy, and their preparation from the corresponding R-substituted indoles by reaction with an N : N-disubstituted formamide in the presence of a condensing agent and alkaline hydrolysis of the product. The aldehydes can be condensed with a nitroalkane to give 3-nitro-alkenyl-indoles, which may be then reduced at the nitro group and the double bond and hydrogenolysed to give 3-(21-aminoalkyl)-hydroxyindoles. In examples 5-benzyloxy-indole is condensed with dimethylformamide in the presence of phosphorus oxychloride and the product hydrolysed to 5-benzyloxyindole-3-aldehyde. Condensation of this with nitroethane gives 5-benzyloxy-3 (21-nitroprop - 11 - enyl) - indole, which is reduced with lithium aluminium hydride to 5 - benzyloxy-3 - (21 - aminopropyl) - indole (isolated as sulphate). Hydrogenolysis then yields the sulphate of 5 - hydroxy - 3 - (21 - aminopropyl)-indole. Serotonin can be made similarly. |
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