Synthesis of diaryloxindoles using a novel protic ionic liquid based on triazole

Document Type : Research Article

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Department of Applied Chemistry, Yasouj University,

10.22034/amnc.2023.413421.1251

Abstract

In this work, three novel 1,4-butane sultone-based Brønsted acidic ionic liquids with hydrogen sulfate conter-anion are prepared. These newly introduced ionic liquids were synthesized from a two-steps reaction. The reaction includes ring opening of 1,4-butane sultone using 1,4-disubstituted 1,2,3-triazole as nitrogen nucleophile sources to obtain zwitterions and then follow by acidification treatment with sulfuric acid to obtain novel Brønsted acidic ionic liquid. The prepared task specific ionic liquids and their stable intermediates were characterized by FT-IR, 1HNMR and 13C-NMR analysis techniques. Their catalytic efficiency was checked for the preparation of symmetric 3,3′-diaryloxindoles compounds. It was found that the introduced acidic ionic liquids are completely green, environmental benign, task specific and have high catalytic stability. These novel acidic ionic liquids are simply separable by extraction from organic phase by solving in water up to eight consecutive runs and give the target products in short reaction times at high yields. This catalyst could be considered as great alternative for old previously reported catalysts.

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