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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.49B [2010] >
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.
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| Page(s): | 818-825 |
| Source: | IJC-B Vol.49B(06) [June 2010]
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