Imidazopyridinium and pyridopyrimidium bromides: synthesis and hydrolysis.

Imidazopyridinium and pyridopyrimidium bromides: synthesis and hydrolysis.
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咪唑并吡啶鎓和吡啶并吡啶溴化物:合成和水解。

DOI:
10.1002/chin.200236144
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发表时间:
2002
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
M. Kurth
M. Kurth
中科院分区:
--
文献类型:
--
作者:
Kevin S. Huang;M. Haddadin;M. Kurth

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对称和不对称2,2'-二吡啶胺与1,2-二溴乙烷和1,3-二溴丙烷的反应分别产生咪唑并吡啶鎓和吡啶并嘧啶鎓溴化物。这些丙酮/CH(2)Cl(2)不溶性、高荧光季铵盐在用甲醇KOH处理后发生加成/开环,得到吡啶-2-酮衍生物。开发了顺序N,N-二烷基化/开环水解/N,N-二烷基化/开环水解策略来构建不对称双(吡啶-2-酮)。
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).