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Author(s): Wang ZY; Wu J
Title: Synthesis of 1H-indol-2-yl-(4-aryl)-quinolin-2(1H)-ones via Pd-catalyzed regioselective cross-coupling reaction and cyclization
Source: TETRAHEDRON 64 (8): 1736-1742
Date: 2008 FEB 18
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China.
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China. Reprint: Wu, J, Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R
China. E-mail: jie_wu@fudan.edu.cn
Author Keywords: 1H-Indole-2-yl-(4-aryl)-quinolin-2(1H)-one; palladium; regioselective
cross-coupling; cyclization
KeyWords Plus: KDR KINASE INHIBITORS; CHANNEL OPENING RELAXANTS; II RECEPTOR
ANTAGONISTS; CORPORAL SMOOTH-MUSCLE; TERMINAL ACETYLENES; ALKYNOL
CYCLOISOMERIZATION; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE-
SYNTHESIS; 2-SUBSTITUTED INDOLES; ERECTILE DYSFUNCTION
Abstract: 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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