Grignard Addition to Quinoxalinium Salt: Synthesis of 1, 2-Dihydro-quinoxaline and 1, 2, 3, 4-Tetrahydroquinoxaline Derivatives
Grignard Addition to Quinoxalinium Salt: Synthesis of 1, 2-Dihydro-quinoxaline and 1, 2, 3, 4-Tetrahydroquinoxaline Derivatives
摘要
Grignard additions to a quinoxalinium salt were studied. Depending on the ratio of the reagents and reaction temperature, 1, 2, 3, 4-tetrahydroquinoxaline and 1, 2-dihydroquinoxaline derivatives could be resulted selectively.
Grignard additions to a quinoxalinium salt were studied. Depending on the ratio of the reagents and reaction temperature, 1, 2, 3, 4-tetrahydroquinoxaline and 1, 2-dihydroquinoxaline derivatives could be resulted selectively.
参考文献9
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9[9]A general procedure for the synthesis of compounds 2 was as follows:A 0.4 mol/L solution of Grignard reagents (4.0 eq.) in ether was added dropwise into the suspension of 1 (1.0 eq.) in THF with stirring under nitrogen at 0℃.After 2 hours,the reaction was quenched with saturated aqueous NH4Cl,followed by usual workup and purification by flash chromatography on silica gel to yield the desired 1,2,3,4-tetrahydroquinoxalines.Compound 2a,1H NMR (300 MHz,CDCl3,δ ppm):6.65-6.43 (m,4H),3.84 (brs,1H),3.06-2.94 (m,5H),1.66-1.39 (m,4H),0.94 (t,3H,J = 4.2 Hz),0.90 (t,3H,J = 4.2 Hz); Compound 2f,1H NMR (300 MHz,CDCl3,δ ppm):7.22-7.03 (m,10H),6.80 (t,1H,J = 7.8 Hz),6.74 (t,1H,J = 6.9 Hz),6.65 (d,1H,J = 7.8Hz),6.60 (d,1H,J = 6.3 Hz),4.36 (d,1H,J = 5.7 Hz),4.26 (d,1H,J = 5.7Hz),4.09 (brs,1H),2.74 (s,3H); 13C NMR (75 MHz,CDCl3,δ ppm):141.9,140.5,136.3,133.8,128.2,127.7,127.5,127.4,119.2,117.6,113.3,111.5,68.9,61.6,37.1.
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