Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes

Author(s): Zahra Abdi Piralghar, Mohammad Mahmoodi Hashemi*, Ali Ezabadi

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 21 , Issue 7 , 2018


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Abstract:

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis.

Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature.

Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions.

Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

Keywords: Ionic liquid, solvent-free conditions, chlorosulfonic acid, N, N, N’, N’-tetramethylethylenediamine, 1, 8-dioxooctahydroxanthenes, aryl aldehyde, dimedone.

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Article Details

VOLUME: 21
ISSUE: 7
Year: 2018
Published on: 15 November, 2018
Page: [526 - 532]
Pages: 7
DOI: 10.2174/1386207321666180828092546
Price: $65

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