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

Autor: Bote IC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Krevlin ZA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Crespo MCF; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Udomphan S; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Levin CT; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Lam CC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Glanzer AM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Hutchinson HL; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Blades AM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., McConnell DL; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Lin C; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Frank JP; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Strutton WR; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Merklin JC; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Sinardo BA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Gueye KJ; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Leiman KV; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Thayaparan A; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Adade JKA; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Martinez NL; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Kramer WW; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States., Majireck MM; Chemistry Department, Hamilton College, 198 College Hill Rd., Clinton, New York 13323, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Nov 22; Vol. 26 (46), pp. 9805-9810. Date of Electronic Publication: 2024 Sep 20.
DOI: 10.1021/acs.orglett.4c02915
Abstrakt: 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.
Databáze: MEDLINE
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