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特定任务离子液体[TMG][Lac]催化超声辅助合成2,4-噻唑烷二酮和若丹宁衍生物

Ultrasound-assisted synthesis of 2,4-thiazolidinedione and rhodanine derivatives catalyzed by task-specific ionic liquid: [TMG][Lac].

作者信息

Sandhu Jagir Singh

机构信息

Department of Chemistry, Punjabi University, Patiala, Punjab, 147 002, India.

出版信息

Org Med Chem Lett. 2013 Mar 3;3(1):2. doi: 10.1186/2191-2858-3-2.

DOI:10.1186/2191-2858-3-2
PMID:23458122
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3599507/
Abstract

BACKGROUND

Synthesized arylidene derivatives of rhodanine and 2,4-thiazolidiendione have potent pharmacological activities, and these are also key substrates for the preparation of clinically used antidiabetics.

FINDINGS

Some 1,1,3,3-tetramethylguanidine-based task-specific ionic liquids (TSILs) 1a-1e were prepared and employed to the catalyzed solvent-free Knoevenagel condensation of 2,4-thiazolidinedione 3a and rhodanine 3b with a variety of aldehydes.

CONCLUSIONS

Best results were obtained with 1,1,3,3-tetramethylguanidine lactate ([TMG][Lac]) 1c. The TSIL used can be easily recovered and recycled, yielding products 4-5 in excellent yields under ultrasonic environment without the formation of any side products or toxic waste.

摘要

背景

若丹宁和2,4-噻唑烷二酮的合成亚芳基衍生物具有强大的药理活性，并且它们也是制备临床使用的抗糖尿病药物的关键底物。

研究结果

制备了一些基于1,1,3,3-四甲基胍的任务特定离子液体（TSILs）1a - 1e，并将其用于催化2,4-噻唑烷二酮3a和若丹宁3b与各种醛的无溶剂Knoevenagel缩合反应。

结论

使用乳酸1,1,3,3-四甲基胍（[TMG][Lac]）1c可获得最佳结果。所使用的TSIL可以很容易地回收和再循环，在超声环境下以优异的产率得到产物4 - 5，且不形成任何副产物或有毒废物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/7495570cc4bd/2191-2858-3-2-i3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/afa04a582b7f/2191-2858-3-2-1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/1f54e2bc7112/2191-2858-3-2-i2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/7495570cc4bd/2191-2858-3-2-i3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/afa04a582b7f/2191-2858-3-2-1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/1f54e2bc7112/2191-2858-3-2-i2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b85/3599507/7495570cc4bd/2191-2858-3-2-i3.jpg

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