Synthesis and biological activities of fused biheterocycles containing indole nucleus: Reactions of 3-(5 '-substituted-3 '-phenylindol-2 '-yl)-4-amino-4,5-dihydro-s-triazol-5-thiones

Abstract

5-(5'-Substituted-3'-phenylindol-2'-yl)-2,3-dihydro-1,3,4-oxadiazol-2-thiones 1a-d on reaction with hydrazine hydrate in ethanol give 3-(5'-substituted-3'-phenylindol-2'-yl)-4-amino-4,5-dihydro-s-triazole-5-thiones 2a-d. These compounds on reaction with phenacyl bromide, chloroacetic acid, cyanogen bromide, carbon disulphide and various aromatic acids furnish 7H-6-phenyl-3-(5'-substituted-3'-phenylindol-2'-yl)-s-triazolo[3,4-b] [1,3,4]thiadiazines 3a-d, 7H-3-(5'-substituted-3'-phenylindol-2'-yl)-s-triazolo [3,4-b][1,3,4]thiadiazin-6(5H)-ones 4a-d, 6-amino-3-(5'-substituted-3'-phenylin-dol-2'-yl)-s-triazololo[3,4-b] [1,3,4] thiadiazoles 5a-d, 3-(5'-substituted-3'-phenylindol-2'-yl)-s-triazolo [3,4-b] [1,3,4]thiadiazole-6(5H)-thiones 6a-d and 6-substituted-3-(5'-substituted-3'-phenylindol-2'-yl)-s-triazolo[3,4-b][1,3,4] thiadiazoles 7a-t. The characterisation of synthesised compounds has been done on the basis of elemental analysis, IR, H-1 NMR and mass spectral data. All the newly synthesised compounds have been screened for their antimicrobial, anthelminthic, anti-inflammatory and anti-catatonic activities.