Imidazopyridinium and pyridopyrimidium bromides: synthesis and hydrolysis.
The reactions of symmetrical and unsymmetrical 2,2'-dipyridylamines with 1,2-dibromoethane and 1,3-dibromopropane give imidazopyridinium and pyridopyrimidium bromides, respectively. These acetone/CH(2)Cl(2)-insoluble, highly fluorescent quaternary ammonium salts undergo addition/ring opening upon treatment with methanolic KOH to give pyridin-2-one derivatives. A sequential N,N-dialkylation/ring-opening hydrolysis/N,N-dialkylation/ring-opening hydrolysis strategy was developed for the construction of unsymmetrical bis(pyridin-2-ones).
Huang
Kevin S
KS
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, USA.
Haddadin
Makhluf J
MJ
Kurth
Mark J
MJ