| 摘要 |
1,164,552. 3-lndolylacetic acid derivatives. MERCK & CO. Inc. 16 Aug., 1967 [20 Aug., 1966], No. 37630/67. Heading C2C. 3-Indolylacetic acid derivatives of the general formula wherein R is a methoxy or dimethylamino group, are prepared by reduction of a hydrazone or semicarbazone derivative of the general formula wherein R<SP>1</SP> is a hydrazono or semicarbazono radical and X is the hydrazinium or semicarbazidium cation. Novel hydrazone and semicarbazone derivatives of the second general formula above are prepared by treatment of an aldehyde of the general formula with hydrazine, optionally in the form of its hydrate, or semicarbazide. Novel aldehydes of the third general formula above are prepared by treatment of the corresponding 2-tosyl-oxymethyl derivative with anhydrous sodium bicarbonate in anhydrous dimethyl sulphoxide. The 2-tosyloxymethyl derivatives are prepared by treatment of 5- hydroxylevulinic acid with dihydropyran, reaction of the resulting 5-hydroxylevulinic acid pyranyl ether ester with p-methoxyphenylhydrazine or p-dimethylaminophenylhydrazine hydrochloride, treatment of the resulting pyranyl 2-pyranyloxymethyl-indole-3-acetate of the general formula with sodium hydride and then p-chlorobenzoyl chloride, reaction of the obtained N-substituted indole of the general formula with concentrated hydrochloric acid and treatment of the resulting 2-hydroxymethyl derivative of the general formula with tosyl chloride. |
