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Synthesis of 2‐O‐Functionalized‐5‐salicyloyl Pyridine Derivatives Catalyzed by 2‐Mercaptobenzimidazole
ChemistrySelect ( IF 2.1 ) Pub Date : 2020-12-01 , DOI: 10.1002/slct.202003748
Abdolali Alizadeh 1 , Akram Bagherinejad 1
Affiliation  

A concise and efficient one‐pot sequential approach for the synthesis of 5‐salicyloyl pyridine frameworks was developed from a reaction of 3‐formylchromones, malononitrile, various alcohols, and 2‐mercaptobenzimidazole as a catalyst. Malononitrile is the nitrogen source in this reaction. In this method, the variety of 2‐alkoxypyridines derivatives containing alkoxy, allyloxy, and acetylene functional groups can increase the bathochromic effect of the λmax of pyridine to the longer wavelengths. According to experimental and theoretical investigations by the DFT method, long‐wavelength bands of 5‐salicyloyl pyridine derivatives related to the HOMO→LUMO and HOMO→LUMO+1 transitions have the ππ* nature and are caused by intramolecular charge transfer from the phenol fragment to the pyridine ring.

中文翻译:

2-巯基苯并咪唑催化2-O-官能化-5-水杨酰基吡啶衍生物的合成

通过3-甲酰基色酮,丙二腈,各种醇和2-巯基苯并咪唑的催化反应,开发出了一种简洁高效的一锅法合成5-水杨酰基吡啶骨架的方法。丙二腈是该反应中的氮源。在该方法中,多种含烷氧基-2- alkoxypyridines衍生物,烯丙氧基和乙炔官能团可以增加的深色效果λ最大吡啶向更长的波长。根据DFT方法的实验和理论研究,与HOMO→LUMO和HOMO→LUMO + 1跃迁相关的5-水杨酰基吡啶衍生物的长波带具有ππ*性质是由分子内电荷从酚片段转移至吡啶环引起的。
更新日期:2020-12-01
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