Imidazopyridinium and pyridopyrimidium bromides: synthesis and hydrolysis

Kevin S Huang; Makhluf J Haddadin; Mark J Kurth

doi:10.1021/jo016387l

Imidazopyridinium and pyridopyrimidium bromides: synthesis and hydrolysis

J Org Chem. 2002 Apr 5;67(7):2382-5. doi: 10.1021/jo016387l.

Authors

Kevin S Huang¹, Makhluf J Haddadin, Mark J Kurth

Affiliation

¹ Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, USA.

PMID: 11925262
DOI: 10.1021/jo016387l

Abstract

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).