Journal
TETRAHEDRON
Volume 59, Issue 40, Pages 7997-8002Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.08.027
Keywords
2-aminobenzyl alcohol; cyclization; oxidative coupling; quinolines; ruthenium catalyst; secondary alcohols
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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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