A versatile strategy for the synthesis of functionalized 2,2'-bi- and 2,2':6',2' '-terpyridines via their 1,2,4-triazine analogues.
A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.
Kozhevnikov
Valery N
VN
Ural State Technical University, 620002, Ekaterinburg, Russia, and Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany. kozhevnikov_v@htf.ustu.ru
Kozhevnikov
Dmitry N
DN
Nikitina
Tatiana V
TV
Rusinov
Vladimir L
VL
Chupakhin
Oleg N
ON
Zabel
Manfred
M
König
Burkhard
B