Process for the preparation of spiro[(4-cyclohexanone)-[3]indol]-2'[1'H]-one derivatives

摘要

The invention relates to a process for the preparation of spiro[(4-cyclohexanone)-[3H]indol]-2'[1'H]-one derivatives of the general formula I wherein R¹ and R² independently stand for hydrogen, C_1-4alkyl, C_1-4alkoxy, C_1-4alkylthio, C_1-4polyfluoroalkyl, C_1-4polyfluoroalkoxy, C_3-7cycloalkyloxy, C_3-7cycloalkylthio, phenoxy, benzyloxy or nitro group-, characterized by reacting an indolin-2-one derivative of the general formula II wherein R¹ and R² are as defined above-with a compound capable for introducing a protective group, selected from 2-tetrahydropyranyl, 1-diethoxy-methylene or C_1-4alkoxycarbonylethyl group, coupling the compound of general formula III, thus obtained-wherein R¹ and R² are as defined above and A stands for a protective group, selected from 2-tetrahydropyranyl, 1-diethoxy-methylene or C_1-4alkoxycarbonylethyl group-with an acrylic acid C_1-4ester, cyclizing the resulting compound of the general formula IV wherein R¹, R² and A are as defined above, R³ stands for C_1-4 alkyl group-, eliminating the -COOR³ group and the A protective group of the keto-ester of general formula V wherein R¹, R², R³ and A are as defined above, optionally without isolation of the compounds of the general formulae IV