Bench-Stable 2-Halopyridinium Ketene Hemiaminals as Reagents for the Synthesis of 2-Aminopyridine Derivatives
Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide 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 S N Ar 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 S N Ar-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.
Source: Organic Letters
Authors: 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
Institution: Hamilton College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4402681679