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

Kevin S. Huang, Makhluf J. Haddadin, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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	https://doi.org/10.1021/jo016387l
State	Published - Apr 5 2002

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo016387l

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title = "Imidazopyridinium and pyridopyrimidium bromides: Synthesis and hydrolysis",

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).",

author = "Huang, {Kevin S.} and Haddadin, {Makhluf J.} and Kurth, {Mark J.}",

year = "2002",

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AU - Huang, Kevin S.

AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

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Y1 - 2002/4/5

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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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