Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source
3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).
Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
Microwave-assisted, palladium-catalyzed carbonylative cyclization - Rapid synthesis of 2-quinolones from unprotected 2-iodoanilines and terminal alkynes
Palladium-catalyzed cyclocarbonylations of 2-iodoanilines with various terminal alkynes have been carried out by the use of commercially available molybdenum hexacarbonyl as a convenient and solid carbon monoxide source. The reactions were conducted at 160 °C for 30 min under microwave irradiation and in the presence of Et3N in THF, affording the corresponding 2-quinolone derivatives in good regioselectivities and yields.
Chen, Jia-Rong,Liao, Jie,Xiao, Wen-Jing
experimental part
p. 331 - 337
(2010/07/08)
Synthesis and pharmacological activities of 3-phenyl-2-(1-piperazinyl)quinolines and related compounds
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Hino,Nagai,Uno
p. 2819 - 2824
(2007/10/02)
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