Synthesis and Antimicrobial Activity of New Triazines, Tetrazines, Thiazinoquinoxalines, Thienotriazepine-imidazo[4, 5-b]quinolines from Isatin Derivatives

Abstract

1-((4-chlorophenyl) (piperazine) methyl) indoline-2, 3-dione (2) were synthesized by using Mannich bases from reacted of isatin (1), p-chlorobenzaldehyde, and piperazine in sodium ethoxide solution. Compounds (1, 2) are used as starting material to prepare many heterocyclic compounds such as: 1-(substituted-piperazine-methyl) indoline-2, 3-dione (3-5), 2-((3-oxo-3H-indole) oxy) acetamide (6), 1, 4-oxazino[2, 3-b]indol-2(3H)-one (7), 2-((1-substituted-2-oxoindolin-3-ylidene) amino) benzoic acid (8-10), 1-(2-bromoacetyl or quinoxaline) indoline-2, 3-dione (11, 12), 2-(dioxoindoline)-2-oxoethyl-carbamimidothioate (13), 1, 3-thiazino[4, 5-b] quinoxaline-indoline-dione (14), imidazo[4, 5-b]quinoline-2-oxoindoline (15), 1, 2, 4-triazino-imidazo[4, 5-b]quinoline-indoline (16), 1, 2, 4, 5-tetrazinoimidazo [4, 5-b] quinoline-indoline (17), and benzothieno-triazepino-imidazo[4, 5-b]quinoline-indoline-amino-benzoic acid (18). The new compounds were evidenced by means of numerous spectroscopic analyses for example IR, NMR, mass spectrum and elemental analysis. All of the synthesized compounds in this search were tested and evaluated as antimicrobial agents. Some of the compounds presented the best efficiency as antimicrobial compared with the cefotaxime sodium and nystatin as standard drugs such as [18, 17, 16, 15 and 14], respectively.