Electrooxidative cyclization of hydroquinolyl alcohols
Electrooxidative cyclization of hydroquinolyl alcohols
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DOI：
10.3987/com-06-10881
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发表时间：
2006-12
期刊：
影响因子：
0.6
通讯作者：
M. Okimoto;Takashi Yoshida;M. Hoshi;K. Hattori;M. Komata;K. Numata;Kenta Tomozawa
中科院分区：
文献类型：
--
作者：
M. Okimoto;Takashi Yoshida;M. Hoshi;K. Hattori;M. Komata;K. Numata;Kenta Tomozawa
在甲醇钠和碘化钾存在下，几种氢喹啉醇、氢异喹啉醇和二氢吲哚醇被电化学氧化。氢喹啉醇和氢异喹啉醇通过氮原子的α-碳与羟基的氧原子之间形成键提供相应的分子内环化产物。相反，吲哚醇经过脱氢得到相应的吲哚醇。据推测，在所有情况下，电氧化都涉及双电子氧化过程。
Several hydroquinolyl, hydroisoquinolyl, and indolinyl alcohols were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide. The hydroquinolyl and hydroisoquinolyl alcohols afforded the corresponding intramolecular cyclization products through the bond formation between the α-carbon of the nitrogen atom and the oxygen atom of the hydroxy group. In contrast, the indolinyl alcohols underwent dehydrogenation to give the corresponding indolyl alcohols. Presumably, in all cases, the electrooxidation involves a two-electron oxidation process.