Journal
TETRAHEDRON
Volume 64, Issue 8, Pages 1736-1742Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.12.003
Keywords
1H-Indole-2-yl-(4-aryl)-quinolin-2(1H)-one; palladium; regioselective cross-coupling; cyclization
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An efficient and novel route for the synthesis of 1H-indol-2-yl-(4-aryl)-quinolin-2(1H)-one 1 via palladium-catalyzed site-selective cross-coupling reaction and cyclization process was described. Reaction of 3 -bromo-4-trifloxy-quinolin-2(1H)-one 3 with arylboronic acid catalyzed by PdCI2(PPh3)(2) afforded 3-bromo-4-aryl-quinolin-2(1H)-one 4, which then reacted with 2-ethynylaniline 5 via Pd-catalyzed Sonogashira coupling and CuI-mediated cyclization leading to the desired 1H-indol-2-yl-(4-aryl)-quinolin-2(1H)-one 1 in good yields. (C) 2007 Elsevier Ltd. All rights reserved.
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