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一种用于快速绿色合成苯并色烯并嘧啶和吡喃并嘧啶的潜在DES催化剂。

A potential DES catalyst for the fast and green synthesis of benzochromenopyrimidines and pyranopyrimidines.

作者信息

Monem Arezo, Habibi Davood, Goudarzi Hadis

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. 2024 Aug 15;14(1):18924. doi: 10.1038/s41598-024-69817-2.

Abstract

A gentisic acid based-Deep Eutectic Solvent (MTPPBr/GA-DES) was synthesized by mixing one mole of methyl triphenylphosphonium bromide (MTPPBr) and one mole of gentisic acid (GA: 2,5-dihydroxy-benzoic acid) based on the eutectic point phase diagram. Then, it was characterized by FT-IR, NMR, densitometer, and TGA/DTA techniques and used as a potent and novel catalyst for the fast and green synthesis of: (i) Five new 2(a-e) and five known 2(f-j) benzo[6,7]chromeno[2,3-d]pyrimidines and (ii) One new (3a) and eleven known 3(b-l) pyrano[2,3-d]pyrimidines, in solvent-free conditions, short reaction times, and high yields. It is important to mention that for the synthesis of 2(a-j), there is only one reference which states that the reaction times are extremely long (720-2400 min), while these times are reduced to approximately 35-50 min in our proposed strategy, indicatinging that the rate of reactions will be 20-48 times faster, which is the clear and most obvious advantage of our approach.

摘要

基于对苯二甲酸的深度共熔溶剂(MTPPBr/GA-DES)是通过根据低共熔点相图将一摩尔甲基三苯基溴化鏻(MTPPBr)和一摩尔对苯二甲酸(GA:2,5-二羟基苯甲酸)混合而合成的。然后,通过傅里叶变换红外光谱(FT-IR)、核磁共振(NMR)、密度计和热重/差热分析(TGA/DTA)技术对其进行了表征,并将其用作一种高效且新颖的催化剂,用于在无溶剂条件下快速绿色合成:(i)五种新的2(a - e)和五种已知的2(f - j)苯并[6,7]色烯并[2,3 - d]嘧啶,以及(ii)一种新的(3a)和十一种已知的3(b - l)吡喃并[2,3 - d]嘧啶,反应时间短且产率高。需要指出的是,对于2(a - j)的合成,仅有一篇参考文献表明反应时间极长(720 - 2400分钟),而在我们提出的策略中,这些时间缩短至约35 - 50分钟,这表明反应速率将快20 - 48倍,这是我们方法明显且最突出的优势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0965/11327281/ed766dec36b1/41598_2024_69817_Fig1_HTML.jpg

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