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Issue 18, 2017
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Efficient catalytic application of a binary ionic liquid mixture in the synthesis of novel spiro[4H-pyridine-oxindoles]

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Abstract

Novel pyrazole-fused spiro[4H-pyridine-oxindoles] were synthesized under the catalysis of the binary ionic liquid mixture [1,1,3,3-tetramethylguanidinium chloride][1-methylimidazolium-3-sulfonate] in solvent-free conditions. The hitherto unreported binary ionic liquid (BIL) was synthesized via an acid–base reaction and has a melting point much lower than that of the moderate temperature ionic liquid, [1,1,3,3-tetramethylguanidinium chloride], it is made from. The synthesis of the spiro-products was realized via a thermodynamically-favored three-component domino reaction between isatins, 1-phenyl-1H-pyrazol-5(4H)-ones, and 4-aminocoumarin. The domino reaction was highly convergent and functional group tolerant, providing a rapid route to synthesize spiro[4H-pyridine-oxindoles] in fairly high yields from simple bench-stable starting materials. No by-products could be resolved from the reaction mixtures under the optimized conditions.

Graphical abstract: Efficient catalytic application of a binary ionic liquid mixture in the synthesis of novel spiro[4H-pyridine-oxindoles]

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Publication details

The article was received on 26 May 2017, accepted on 04 Aug 2017 and first published on 07 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ01858D
Citation: New J. Chem., 2017,41, 10291-10298
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    Efficient catalytic application of a binary ionic liquid mixture in the synthesis of novel spiro[4H-pyridine-oxindoles]

    S. Yaghoubi Kalurazi, K. Rad-Moghadam and S. Moradi, New J. Chem., 2017, 41, 10291
    DOI: 10.1039/C7NJ01858D

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