A convenient route for efficient conversion of unprotected anthranilic acids into the corresponding N-(2-aminoarylacyl)benzotrazoles is described. N-(2-Aminoarylacyl)-benzotrazoles have been successfully used to synthesize primary, secondary and tertiary anthranilamides in high yields (71-96%).
Sixteen new compounds, including novel five-membered heterocyclic systems (pyrrole, thiophene, or furan) linked to imidazole, thiazole, or quinoline rings are reported. The intermediate 1,4-diketones were synthesized via the Stetter reaction in the presence of thiazolium salt as a catalyst. Cyclization reactions of the 1,4-dicarbonyl compounds with polyphosphoric acid, ammonium acetate or Lawesson's reagent by the Paal-Knorr synthesis, afforded unknown 2,5-disubstituted furan, pyrrole, or thiophene compounds in moderate yields, respectively. The structures of the synthesized compounds were confirmed by IR, 1 H NMR, 13 C NMR, and elemental analysis.
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