Bench-Stable 2-Halopyridinium Ketene Hemiaminals as Reagents for the Synthesis of 2-Aminopyridine Derivatives.

IF 5.4 3区 材料科学 Q2 CHEMISTRY, PHYSICAL
Isabelle C Bote, Zoe A Krevlin, Maria Christina F Crespo, Sudchananya Udomphan, Carolyn T Levin, Christie C Lam, Amy M Glanzer, Holly L Hutchinson, Alisha M Blades, Danielle L McConnell, Crystal Lin, John P Frank, William R Strutton, Jordan C Merklin, Beau A Sinardo, Khady J Gueye, Karly V Leiman, Ashley Thayaparan, Joel K A Adade, Nestor L Martinez, Wesley W Kramer, Max M Majireck
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引用次数: 0

Abstract

2-Chloro-1-(1-ethoxyvinyl)pyridinium triflate and several other bench-stable N-(1-alkoxyvinyl) 2-halopyridinium triflates have been developed as reagents for the synthesis of valuable 2-aminopyridine scaffolds via unusually mild SNAr substitutions with amine nucleophiles. Advantages of this approach include an operationally simple mix-and-stir procedure at room temperature or mild heat and ambient atmosphere and without the need for transition metal catalysts, coupling reagents, or high-boiling solvents. The stable N-(1-ethoxyvinyl) moiety serves as a dual SNAr-activating group and pyridine N-protecting group that can be cleaved under thermal, acidic, or oxidative conditions. Preliminary results of other nucleophilic substitutions using oxygen-, sulfur-, and carbon-based nucleophiles are also demonstrated.

Abstract Image

作为 2-氨基吡啶衍生物合成试剂的台式稳定 2-卤代吡啶鎓烯酮半二胺。
作为试剂,2-氯-1-(1-乙氧基乙烯基)吡啶鎓三氟化物和其他几种稳定的 N-(1-烷氧基乙烯基)2-卤代吡啶鎓三氟化物已被开发出来,用于通过异常温和的 SNAr 与胺类亲核剂的取代反应合成有价值的 2-氨基吡啶支架。这种方法的优点包括操作简单,可在室温或微热环境下进行混合搅拌,无需过渡金属催化剂、偶联试剂或高沸点溶剂。稳定的 N-(1-乙氧基乙烯基)分子具有 SNAr 活性基团和吡啶 N 保护基团的双重作用,可以在热、酸或氧化条件下裂解。此外,还展示了使用氧、硫和碳基亲核物进行其他亲核取代的初步结果。
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来源期刊
ACS Applied Energy Materials
ACS Applied Energy Materials Materials Science-Materials Chemistry
CiteScore
10.30
自引率
6.20%
发文量
1368
期刊介绍: ACS Applied Energy Materials is an interdisciplinary journal publishing original research covering all aspects of materials, engineering, chemistry, physics and biology relevant to energy conversion and storage. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials, engineering, physics, bioscience, and chemistry into important energy applications.
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