Regioselective Amination or Alkoxylation of Halogenated Amino-, Thio- or Alkoxypyridines via Pyridyne Intermediates.

Autor: Heinz, Benjamin, Djukanovic, Dimitrije, Siemens, Fiona, Idriess, Mohamed, Martin, Benjamin, Knochel, Paul
Předmět:
Zdroj: Synthesis; Nov2022, Vol. 54 Issue 22, p5055-5063, 9p
Abstrakt: The treatment of 3-halopyridines (Cl, Br) bearing an R-substituent in position 2 (R = OEt, NEt2 , N -piperidyl, or SEt) or in position 5 (R = OMe, OEt, SEt, NMe2 , NEt2 , or aryl) with KHMDS and an amine at 25 °C for 12 hours in THF provided regioselectively 3- and 4-aminated pyridines in 56–90% yields. The reaction of 3-bromo-2-diethylaminopyridine with various alcohols in the presence of t -BuOK/18-crown-6 in THF at 80 °C for 20–60 hours gave various 4-alkoxy-2-diethylaminopyridines in 61–81% yields. These substitution reactions were proposed to proceed via pyridyne intermediates. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index