Synthesis of New Triazole and Aza-andbeta;-lactam Compounds Derived from o-(Npropargyl)-sulfonamido Benzoic Acid of Possible Biological Activity

Ahmed W Naser; Muthanna S Farhan; Kany A Abdulqader

Abstract

Synthesis of New Triazole and Aza-β-lactam Compounds Derived from o-(Npropargyl)-sulfonamido Benzoic Acid of Possible Biological Activity

Author(s): Ahmed W Naser, Muthanna S Farhan, Kany A Abdulqader

A variety of new triazole and Aza-β-lactam derivatives derived from o-(N-propargyl) sulfonamido benzoic acid (1a) were synthesized. Firstly, reaction of compound (1a) with absolute ethanol, in the presence concentrated H₂SO₄ gave ethyl-o-(N-propargyl)sulfoamido benzoate (2a). Subsequently, the produced react with 80% hydrazine hydrate gave o-(N-propargyl)sulfonamido benzohydrazide (3a). The cyclization of (3a) with carbon disulfide and hydrazine hydrate (80%) in presence potassium hydroxide gave o-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-N-propargyl benzene sulfonamide compound (4a). N-propargyl-o-[N\-sulfamidobenzoyl] hydrazine carboxamide (5a) was obtained by reaction of (3a) with Phenyl isocyanates. The cyclization of compound (5a) with 30% NaOH gave 3-hydroxy-4-phenyl-1,2,4-triazole compound (6a). The Schiff bases (7a-b) were obtained by condensation of (3a) with 4-(N,N-dimethyl amino)benzaldehyde and p-nitrobenzaldehyde. Aza-β-lactam compounds (8a-b) were prepared by the cycloaddition of Schiff-bases (7a-b) with phenyl isocyanate via [2+2] cycloaddition reaction. The newly prepared compounds were identified by (FTIR), (¹H-NMR) and their physical properties were measured. The compounds were tested for their biological activity, some compound was active and others were not.

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