Solid-phase synthesis of thiazolo[4,5-b]pyridine derivatives using Friedländer reaction.
Traceless solid-phase synthesis of 2,5,6,7-tetrasubstituted thiazolo[4,5-b]pyridine derivatives is described. Thorpe-Ziegler type cyclization of solid supported cyanocarbonimidodithioate with alpha-halo ketones afforded thiazole resin, which were converted to the desired thiazolopyridine resin by the Friedländer protocol under microwave irradiation conditions. After oxidation of sulfides to sulfones, nucleophilic desulfonative substitution with amines gave the target thiazolo[4,5-b]pyridine derivatives in good overall yields.
Lee
Taeho
T
Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology, Yuseong-gu, Daejeon, Korea. taeholee@krict.re.kr
Lee
Doohyun
D
Lee
Ill Young
IY
Gong
Young-Dae
YD
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D011725:Pyridines; D013844:Thiazoles