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/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).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2382-2385 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 67 |
| Issue number | 7 |
| DOIs | |
| State | Published - Apr 5 2002 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Imidazopyridinium and pyridopyrimidium bromides : Synthesis and hydrolysis. / Huang, Kevin S.; Haddadin, Makhluf J.; Kurth, Mark J.
In: Journal of Organic Chemistry, Vol. 67, No. 7, 05.04.2002, p. 2382-2385.Research output: Contribution to journal › Article
}
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).
UR - http://www.scopus.com/inward/record.url?scp=0037023412&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037023412&partnerID=8YFLogxK
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 -