Cyclization of 4-hydroxy-3-hydroxyalkylcarbostyrils under mitsunobu conditions

Cyclization of 4-hydroxy-3-hydroxyalkylcarbostyrils under mitsunobu conditions
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DOI:
10.1081/scc-200030595
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发表时间:
2004-09-01
影响因子:
2.1
通讯作者:
Coppola, GM
Coppola, GM
中科院分区:
化学4区
文献类型:
--
作者:
Coppola, GM

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4-羟基-3-羟烷基-1-甲基-2(1H)喹啉酮与Ph3P/DEAD的反应根据链长产生C-或O-环化产物。羟乙基仅产生螺环丙基喹啉酮 6,而羟丙基仅产生吡喃喹啉酮 8。羟丁基产生螺环环戊基喹啉酮 11 和氧杂吡啶喹啉酮 10 的 2:1 混合物。
Reaction of 4-hydroxy-3-hydroxyalkyl-1-methyl-2(1H)quinolinones with Ph3P/DEAD gives either C- or O-cyclized products depending on chain length. Hydroxyethyl produces only spiro cyclopropylquinolinone 6, whereas hydroxypropyl affords only pyranoquinolinone 8. Hydroxybutyl gives a 2:1 mixture of spiro cyclopentylquinolinone 11 and oxepinoquinolinone 10.