1253932-75-0Relevant academic research and scientific papers
Synthesis, characterization and biological evaluation of some heterocyclic compounds containing ethoxyphthalimide moiety via key intermediate 6-chloro 1,3 benzothiazole 2-amine
Sain, Devendra Kr.,Thadhaney, Bhawana,Joshi, Ajit,Hussain, Nasir,Talesara, Ganpat L.
experimental part, p. 818 - 825 (2011/02/23)
New and simple synthetic methods for the synthesis of ethyl 8-chloro-4(4-substitutedphenyl)-2-[(N-ethoxyphthalimido)amino]-4H-pyrimido[2, 1-b][1,3] benzothiazole-3-carboxylate 5a-d and 6-chloro-N-[3-{2-(4- substitutedphenyl)ethenyl}-1-N-ethoxyphthalimidoquinoxalin-2(1N)-ylidene]-1, 3-benzothiazol-2-amine 10a-d are described. 4-Chloroaniline 1 is converted to 6-chloro-1,3-benzothiazol-2-amine 2 by reaction with KSCN and Br2. Compound 2 acts as key intermediate for both the series of final compounds. In one pathway, 2 is converted to corresponding pyrimidothiazoles 4a-d by treatment with ethyl arylidinecyanoacetate 3a-d, which on condensation with phthalimidoxyethyl bromide 6 gives 5a-d. In a parallel route, reaction of 2 with 3-[2-(4-substituted phenyl)ethenyl]quinoxalin-2(1H)-one 8a-d affords 6-chloro-iV-[3-{2-(4-substituted phenyl)ethenyl} quinoxalin-2(1H)-ylidene]-1,3- benzothiazol-2-amine 9a-d which on condensation with phthalimidoxyethyl bromide 6, yields final compound 10a-d. Structure elucidation is accomplished by elemental analysis and spectral data of the synthesized compounds. Final compounds 5a-d and 10a-d have been screened in vitro for their antimicrobial activity against different strains of bacteria and fungi.
