220400-12-4Relevant academic research and scientific papers
Coupling of consecutive pyridine ring units for oligopyridine synthesis
Uenishi, Jun'ichi,Ueno, Tetsuya,Hata, Sin'ichiro,Nishiwaki, Kenji,Tanaka, Takakazu,Wakabayashi, Shoji,Yonemitsu, Osamu,Oae, Shigeru
, p. 341 - 351 (2007/10/03)
The reaction of 2-ethylsulfinyl-6-(ethylthio)pyridine (2), 6- ethylsulfinyl-6'-ethylthio-2,2'-bipyridine (6), and 6-ethylsulfinyl-6'''- ethylthio-2,2':6',2'':6'',2'''-quaterpyridine (10) with methylmagnesium bromide gave symmetric oligopyridines 6,6'-bis(ethylthio)-2,2'-bipyridine (4), 6,6'''-bis(ethylthio)-2,2':6',2'':6'',2'''-quaterpyridine (8), and 6,6'''''''-bis(ethylthio)- 2,2':6',2'':6'',2''':6''',2'''':6'''',2''''':6''''',2'''''':6'''''',2''''''- octipyridine (12) in respective yields of 70, 56, and 3%. On the other hand, the reaction of 6 and 10 with 2-(6-bromopyridinyl)lithium and 6-(2,2'- bipyridinyl)lithium gave the corresponding unsymmetric oligopyridines (15, 16, 13, and 19). The reaction with chiral (S)-2-{6-[1-(tert- butyldimethylsiloxy)ethyl]pyridinyl}lithium gave optically active oligopyridines (17) and (18) in 78 and 58% yields, respectively.
