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基于缬氨酸-丙二酸的离子液体作为噻唑并嘧啶绿色合成的高效催化剂的制备、表征及应用

Preparation, characterization, and application of a valine-malonic acid based-DES as a potent catalyst for the green synthesis of thiazolopyrimidines.

作者信息

Dehnokhalaji Nastaran, Habibi Davood, Monem Arezo, Ranjbaran Afagh

机构信息

Department of Organic Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University, Hamedan, 6517838683, Iran.

出版信息

Sci Rep. 2025 May 31;15(1):19139. doi: 10.1038/s41598-025-03630-3.

DOI:10.1038/s41598-025-03630-3
PMID:40450071
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12126544/
Abstract

Based on the eutectic point phase diagram, a novel natural deep eutectic solvent (VAL/MAL-DES) was prepared by a mixture of one mole of valine (VAL) and one mole of malonic acid (MAL), and characterized by the eutectic points, FT-IR, HNMR, TGA/DTA and densitometer techniques. Then, it was used as a novel and capable catalyst for the green synthesis of thiazolo[3,2-a]pyrimidines via a one-pot four-component condensation reaction of 4-hydroxycoumarin, 2-amino-6-methylbenzothiazole, morpholine, and aldehydes at 80 °C with high yield and short reaction time.

摘要

基于低共熔点相图，通过将一摩尔缬氨酸（VAL）和一摩尔丙二酸（MAL）混合制备了一种新型天然低共熔溶剂（VAL/MAL-DES），并采用低共熔点、傅里叶变换红外光谱（FT-IR）、核磁共振氢谱（HNMR）、热重/差示热分析（TGA/DTA）和密度计技术对其进行了表征。然后，将其用作一种新型且高效的催化剂，用于在80℃下通过4-羟基香豆素、2-氨基-6-甲基苯并噻唑、吗啉和醛的一锅四组分缩合反应绿色合成噻唑并[3,2-a]嘧啶，反应产率高且反应时间短。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/ed6323e87616/41598_2025_3630_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/c322dfe7004a/41598_2025_3630_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/e7b70c69c485/41598_2025_3630_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/a1a4caaade51/41598_2025_3630_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/5b364e17713f/41598_2025_3630_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/d3f9b34f06cc/41598_2025_3630_Fig3a_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/c54e8c2c3f11/41598_2025_3630_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/9f454ef417bf/41598_2025_3630_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/d956b4473920/41598_2025_3630_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/ed6323e87616/41598_2025_3630_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/c322dfe7004a/41598_2025_3630_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/e7b70c69c485/41598_2025_3630_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/a1a4caaade51/41598_2025_3630_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/5b364e17713f/41598_2025_3630_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/d3f9b34f06cc/41598_2025_3630_Fig3a_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/c54e8c2c3f11/41598_2025_3630_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/9f454ef417bf/41598_2025_3630_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/d956b4473920/41598_2025_3630_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a984/12126544/ed6323e87616/41598_2025_3630_Fig5_HTML.jpg

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本文引用的文献

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Sci Rep. 2025 Mar 3;15(1):7508. doi: 10.1038/s41598-025-90953-w.
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Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl⋅6HO deep eutectic solvent.盐酸苯海拉明 - 氯化钴·6水合物低共熔溶剂催化高效合成新型噻二唑并[2,3 - b]喹唑啉 - 6 - 酮
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An acid-based DES as a novel catalyst for the synthesis of pyranopyrimidines.
一种用于合成吡喃嘧啶的新型催化剂——酸碱深共熔溶剂
Sci Rep. 2023 Oct 21;13(1):18009. doi: 10.1038/s41598-023-45352-4.
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Synthesis and biological evaluation of new derivatives of thieno-thiazole and dihydrothiazolo-thiazole scaffolds integrated with a pyrazoline nucleus as anticancer and multi-targeting kinase inhibitors.噻吩并噻唑和二氢噻唑并噻唑支架与吡唑啉核整合的新型衍生物作为抗癌和多靶点激酶抑制剂的合成及生物学评价
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Design, synthesis and molecular docking of new pyrazole-thiazolidinones as potent anti-inflammatory and analgesic agents with TNF-α inhibitory activity.设计、合成及分子对接新型吡唑并噻唑烷酮类化合物作为具有 TNF-α 抑制活性的新型强效抗炎和镇痛药物。
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New thiazolopyrimidine as anticancer agents: Synthesis, biological evaluation, DNA binding, molecular modeling and ADMET study.新型噻唑并嘧啶类抗癌剂的合成、生物评价、DNA 结合、分子模拟及 ADMET 研究。
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