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IJC-B Vol.46B(05) [May 2007] >


Title: Synthesis and characterization of some alkoxyphthalimide derivatives of benzotriazolylthiadiazoles and benzotriazolylthiazolidinones
Authors: Ojha, Swati
Ameta, Usha
Dhakar, Neelam
Talesara, G L
Keywords: Benzotriazole
Carbothioamide
Thiadiazole
ω-Bromoalkoxyphthalimide
Condensation
Thiazolidinone
Thiosemicarbazide
Issue Date: May-2007
Publisher: CSIR
IPC CodeInt.Cl.⁸ C 07 D
Abstract: In the present investigation newer and simple synthetic methods of 5-(1,2,3-benzotriazol-1-yl-methyl)-N-alkoxyphthalimido-1,3,4-thiadiazol-2-amines 5a-b and 2-[(1,2,3-benzotriazolyl)acetohydrazido]-3-N-alkoxyphthalimido-5-arylidene-1,3-thiazolidin-4-ones 9a-h are described. Benzotriazole 1 is converted to carbothioamide 3 by the reaction with ethylchloroacetate followed by thiosemicarbazide. Compound 3 has acted as key intermediate for both series of the final compounds. In one pathway, 3 is converted to corresponding thiadiazole 4 by treatment with Conc. H₂SO₄ and NH₃, which on condensation with ω-bromoalkoxyphthalimide 10a-b gives 5a-b. In an alternative route reaction of 3 with chloroacetic acid and aromatic aldehydes 7a-d has afforded the formation of 2-[(1,2,3-benzotriazolyl)acetohydrazido]-5-arylidene-1,3-thiazolidin-4-ones 8a-d, which are further treated with 10a-b to furnish the final compounds 9a-h. Structural elucidation is accomplished by IR, ¹H NMR and mass spectral data of the synthesized compounds.
Page(s): 860-865
ISSN: 0376-4699
Source:IJC-B Vol.46B(05) [May 2007]

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