Monem Arezo, Habibi Davood, Goudarzi Hadis
Department of Organic Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University, Hamedan, 6517838683, Iran.
Sci Rep. 2024 Aug 15;14(1):18924. doi: 10.1038/s41598-024-69817-2.
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.
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。