Synthesis of 2-azaindolizines by using an iodine-mediated oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides and an investigation of their photophysical properties.
Iodine-mediated, oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides serves as an efficient and versatile method for the preparation of 2-azaindolizines (imidazo[1,5-a]pyridines) and rare 2-azaindolizine sulfur-bridged dimers. The 2-azaindolizines prepared in this manner are readily converted to a variety of fluorescent compounds by using transition-metal-catalyzed cross-coupling reactions. [reaction: see text].
Shibahara
Fumitoshi
F
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan. fshiba@gifu-u.ac.jp
Kitagawa
Asumi
A
Yamaguchi
Eiji
E
Murai
Toshiaki
T
D001372:Aza Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D010084:Oxidation-Reduction; D010777:Photochemistry; D011725:Pyridines / Q000138:chemical synthesis*; D013455:Sulfur / Q000737:chemistry; D013854:Thioamides / Q000138:chemical synthesis*
D001372:Aza Compounds; D007212:Indolizines; D008670:Metals; D011725:Pyridines; D013854:Thioamides; D013455:Sulfur; D007455:Iodine