Synthesis and biological activities of novel 2-(5 '-substituted-3 '-phenylindole-2 '-yl)-1,3,4-oxadiazino[5,6-b]indole and 3-(5 '-substituted-3 '-phenylindole-2 ' amido)spiro-(indol-3 '',2-thiazolidine)-2 '',4-diones

Abstract

Condensation of 5-subtituted-3-phenylindole-2-carbohydrazides 1a-d with isatin 2 gives isatin-beta-(5'-substitued-3'-phenylindole-2'-carbonylhydrazones) 3a-d, which on treatment with H2SO4 undergo cyclodehydration to yield 2-(5'-substituted-3'-phenylindole-2'-yl)-1,3,4-oxadiazino[5,6-b]indoles 4a-d. The hydrazones 3a-d on treatment with mercaptoacetic acid in DMF in the presence of anhydrous ZnCl2 afford 3-(5'-substituted-3'-phenylindol-2'-amido)spiro-(indole-3",2-thiazolidine)-2",4-diones 5a-d. The characterisation of synthesised compounds have been done on the basis of elemental analysis, IR, H-1 NMR and mass spectral data. All the synthesised compounds are tested for their biological (antibacterial, antifungal, anthelmintic and anticonvulsant) activities.