Tetrahedron p. 5111 - 5118 (1991)
Update date:2022-07-31
Sakamoto, Takao
Kondo, Yoshinori
Uchiyama, Daishi
Yamanaka, Hiroshi
3-Substituted 5-(tributylstannyl)isoxazoles were newly synthesized by the 1,3-dipolar cyctoadditton of nitrile oxides to tributylethynylstannane. The iodination and the palladium-catalyzed benzoylation of 5-(tributylstannyl)-3-methylisoxazolegave 5-iodo-3-methylisoxazole and 3-methyl-5-isoxazolyl phenyl ketone in satisfactory yields, respectively. The palladium-catalyzed cross-coupling reaction of the stannylisoxazole with 2-bromonitrobenzene followed by the catalytic hydrogenation over Raney nickel resulted in the formation of 2-methyll-4(1H)-quinolinone in 57% overall yield.
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