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

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 approac...

Full description

Saved in:

Bibliographic Details
Published in:	Organic letters Vol. 26; no. 46; pp. 9805 - 9810
Main Authors:	Bote, Isabelle C., Krevlin, Zoe A., Crespo, Maria Christina F., Udomphan, Sudchananya, Levin, Carolyn T., Lam, Christie C., Glanzer, Amy M., Hutchinson, Holly L., Blades, Alisha M., McConnell, Danielle L., Lin, Crystal, Frank, John P., Strutton, William R., Merklin, Jordan C., Sinardo, Beau A., Gueye, Khady J., Leiman, Karly V., Thayaparan, Ashley, Adade, Joel K. A., Martinez, Nestor L., Kramer, Wesley W., Majireck, Max M.
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 22-11-2024
Subjects:	Letter
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/acs.orglett.4c02915