TY - JOUR
T1 - Imidazopyridinium and pyridopyrimidium bromides
T2 - Synthesis and hydrolysis
AU - Huang, Kevin S.
AU - Haddadin, Makhluf J.
AU - Kurth, Mark J.
PY - 2002/4/5
Y1 - 2002/4/5
N2 - 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/CH2Cl2 -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).
AB - 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/CH2Cl2 -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).
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U2 - 10.1021/jo016387l
DO - 10.1021/jo016387l
M3 - Article
C2 - 11925262
AN - SCOPUS:0037023412
VL - 67
SP - 2382
EP - 2385
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 7
ER -