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IJC-B Vol.49B(06) [June 2010] >


Title: Synthesis, characterization and biological evaluation of some heterocyclic compounds containing ethoxyphthalimide moiety via key intermediate 6-chloro 1,3 benzothiazole 2-amine
Authors: Sain, Devendra Kr
Thadhaney, Bhawana
Joshi, Ajit
Hussain, Nasir
Talesara, Ganpat L
Keywords: Ethoxyphthlimidoquinoxaline
arylidene
benzo¬thiazol
phthalimidoxyethyl bromide
spectral data
antimicrobial activity
Issue Date: Jun-2010
Publisher: CSIR
Abstract:  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(1H)-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-N-[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.
Page(s): 818-825
Source:IJC-B Vol.49B(06) [June 2010]

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