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一种利用新型不对称取代双硫脲系列作为可行前体来合成双-2-亚氨基噻唑烷-4-酮的可持续策略。

A sustainable strategy for the synthesis of bis-2-iminothiazolidin-4-ones utilizing novel series of asymmetrically substituted bis-thioureas as viable precursors.

作者信息

Ahmed Arafa Wael Abdelgayed, Ibrahim Hamada Mohamed

机构信息

Chemistry Department, College of Science, Jouf University P.O. Box 72341 Sakaka Aljouf Kingdom of Saudi Arabia

Chemistry Department, Faculty of Science, Fayoum University P.O. Box 63514 Fayoum City Egypt.

出版信息

RSC Adv. 2018 Mar 15;8(19):10516-10521. doi: 10.1039/c8ra01253a. eCollection 2018 Mar 13.

DOI:10.1039/c8ra01253a
PMID:35540444
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9078912/
Abstract

A novel series of asymmetrically substituted bis-thioureas has been synthesized in an effective pattern the reaction of diamines with isothiocyanates utilizing the ultrasonic irradiation as a sustainable energy source. This reaction performs well at mild conditions to give the products in quantitative yields for a broad scope of substrates. The bis-thiourea derivatives are used for the design of unprecedented series of bis-2-iminothiazolidin-4-ones promoted by the ultrasonic irradiation. The reaction affords the formation of regioselective products, which depends on the p s of the diamines. The diamine linked to the thiourea possessing lower p is involved in the imino part, and the diamine having higher p is a part of the other heterocyclic nitrogen. Moreover, this new strategy has excellent environmental parameters, demonstrating that this protocol is a green and sustainable process.

摘要

通过一种有效的方式合成了一系列新型的不对称取代双硫脲,即利用超声辐射作为可持续能源,使二胺与异硫氰酸酯发生反应。该反应在温和条件下表现良好,对于广泛的底物都能以定量产率得到产物。双硫脲衍生物用于设计由超声辐射促进的前所未有的双-2-亚氨基噻唑烷-4-酮系列。该反应生成区域选择性产物,这取决于二胺的pKa值。与具有较低pKa值的硫脲相连的二胺参与亚氨基部分,而具有较高pKa值的二胺是另一个杂环氮的一部分。此外,这种新策略具有出色的环境参数,表明该方案是一个绿色且可持续的过程。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/d1ca4ee70ba2/c8ra01253a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/f9910535801a/c8ra01253a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/55ddbad1e2ab/c8ra01253a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/f5eff678745f/c8ra01253a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/d1ca4ee70ba2/c8ra01253a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/f9910535801a/c8ra01253a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/55ddbad1e2ab/c8ra01253a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/f5eff678745f/c8ra01253a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b5c/9078912/d1ca4ee70ba2/c8ra01253a-s4.jpg

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