CONDENSED HETEROAROMATIC RING-SYSTEMS .19. SYNTHESIS AND REACTIONS OF 5-(TRIBUTYLSTANNYL)ISOXAZOLES

被引:52
作者
SAKAMOTO, T [1 ]
KONDO, Y [1 ]
UCHIYAMA, D [1 ]
YAMANAKA, H [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,AOBA KU,SENDAI,MIYAGI 980,JAPAN
关键词
D O I
10.1016/S0040-4020(01)87123-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Substituted 5-(tributylstannyl)isoxazoles were newly synthesized by the 1,3-dipolar cycloaddition of nitrile oxides to tributylethynylstannane. The iodination and the palladium-catalyzed benzoylation of 5-(tributylstannyl)-3-methylisoxazole gave 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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收藏
页码:5111 / 5118
页数:8
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