Synthesis and antiparkinsonian activity of some new adamantyl thiazolidinonyl/azeti¬dinonyl indole derivatives

Abstract

Several 3-adamantylimino-2-(substitutedphenyl)-5-substituted-1<i style="">H</i>-indoles <b style="">1a-h </b>have been prepared by the reaction of various 2-substitutedphenyl-5-substitutedindol-3-aldehydes with amanta­dine. Cycloaddition of <b style="">1a-h</b> with thioglycolic acid in presence of anhydrous zinc chloride yielded 3-adamantyl-2-(2-(2-substi­tutedphenyl)-5-substituted-1<i style="">H</i>-indol-3-yl)thiazolidin-4-ones <b style="">2a-h</b>. Compounds<b style=""> 1a-h</b> on reaction with chloro acetyl chloride in presence of triethyl amine give 1-adamantyl-3-chloro-4-(2- (2-substitutedphenyl)-5-substituted-1<i style="">H</i>-indol-3-yl)azetidin-2-ones <b style="">3a-h</b>. Structures of the newly synthesized compounds have been delineated by elemental and spectral (IR, ¹H NMR and mass) analysis.