Oxidative activation of dihydropyridine amides to reactive acyl donors?
Organic & Biomolecular Chemistry Pub Date: 2014-10-31 DOI: 10.1039/C4OB01931H
Abstract
Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields.
Recommended Literature
- [1] Emergence of microfluidic wearable technologies Joo Chuan Yeo,KenryLab Chip, 2016,16, 4082-4090 10.1039/C6LC00926C
- [2] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
- [3] Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies Jason WanLab Chip, 2020,20, 4528-4538 10.1039/D0LC00881H
- [4] Dissociative dynamics of O2 on Ag(110)? Ivor Lon?ari?Phys. Chem. Chem. Phys., 2015,17, 9436-9445 10.1039/C4CP05900J
- [5] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [6] Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling?? Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang ChiJ. Mater. Chem. A, 2021,9, 2111-2119 10.1039/D0TA07814J
- [7] Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process? Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying ChenJ. Mater. Chem. A, 2014,2, 18831-18837 10.1039/C4TA03994G
- [8] Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. ChalmersAnalyst, 2005,130, 514-527 10.1039/B412723D
- [9] Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field XuxinCheng,XiaomingChen,PengyuanFan 10.1007/s10832-022-00283-w
- [10] Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications Partha Laskar,Christine DufèsNanoscale Adv., 2021,3, 6007-6026 10.1039/D1NA00536G
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)