Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines

被引:150
作者
Cho, CS [2 ]
Kim, BT
Choi, HJ
Kim, TJ
Shim, SC
机构
[1] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea
关键词
2-aminobenzyl alcohol; cyclization; oxidative coupling; quinolines; ruthenium catalyst; secondary alcohols;
D O I
10.1016/j.tet.2003.08.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Aminobenzyl alcohol is oxidatively coupled and cyclized with secondary alcohols in dioxane at 80degreesC in the presence of a catalytic amount of RuCl2(PPh3)(3) and KOH along with 1-dodecene as a sacrificial hydrogen acceptor to give the corresponding quinolines in good yields. The cyclization is applicable to a wide range of alkyl(aryl) and alkyl(alkyl) carbinols. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of both substrates to carbonyl compounds, cross aldol reaction, and cyclodehydration. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码:7997 / 8002
页数:6
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