Preparation method of multi-substituted tetrahydroquinoxaline derivative
A technology of tetrahydroquinoxaline and compound is applied in the field of preparation of polysubstituted tetrahydroquinoxaline derivatives, and can solve the problems of unfavorable industrial production, flammability and explosion of hydrogen and high danger
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Embodiment 1
[0024] Example 1 Preparation of compound 3a: Weigh out o-aminophenylimine 2a (0.10 mmol) and rhodium acetate (0.001 mmol), and add 2.0 mL of redistilled dichloromethane to each reaction tube. Increase the temperature and keep the reaction temperature at 40℃. Dissolve methyl aryldiazoacetate 1a (0.15mmol) in 2mL of distilled dichloromethane and inject it into the reaction system through a peristaltic pump for 1 hour. The reaction was continued at ℃ for 3h, and the reaction was over. The solvent was removed by rotary evaporation at 40 ℃, and then column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 ~ 1:5) was used to separate the tetrahydroquinoxaline compounds 3a, the yield is 75%, and the dr is 95:5, see Table 1.
[0025] .
[0026] Characterization of the product tetrahydroquinoxaline compound 3a: 1 HNMR(300MHz, CDCl 3 ) δ 8.60(s,1H), 7.57-7.54(m,2H),7.34-7.31(m,3H),6.92-6.57(m,8H),5.30(s,1H),5,19( s, 1H), 4.07 (s, 1H ), 3.63 (s, 3H ); 13 C NMR (75MHz, CDCl 3 )...
Embodiment 2-12
[0027] Examples 2-12 Preparation of compounds (3b to 3l).
[0028] Examples 2-12 are the same as in Example 1. See Table 1 for the change of substituents, compound number, d.r. value, yield, etc. in the reaction.
[0029] Table 1.
[0030] Example1 / R4
2 / R 1 / R 2 / R 3
productd.r. Yield(%) 11a / C 6 H 4
2a / H / H / H3a 95:575 21a / C 6 H 4
2b / H / H / CH 3
3b 95:563 31a / C 6 H 4
2c / H / H / NO 2
3c 95:585 41a / C 6 H 4
2d / H / H / COC 6 H 5
3d 95:583 51a / C 6 H 4
2e / H / OCH 3 / H
3e 95:577 61a / C 6 H 4
2f / NO 2 / H / H
3f 95:595 71a / C 6 H 4
2g / Br / H / H3g 95:581 81a / C 6 H 4
2h / Cl / H / H 3h 95:580 91b / 4-MeOC 6 H 4
2a / H / H / H3i 95:567 101c / 4-BrC 6 H 4
2a / H / H / H3j 95:563 111d / 3-BrC 6 H 4
2a / H / H / H3k 95:570 121e / 3-ClC 6 H 4
2a / H / H / H3l 95:575
[0031] The product tetrahydroquinoxaline compounds 3b to 3l are characterized as follows:.
[0032] Characterization of product 3b: 1 H NMR (300 MHz, CDCl 3 ) δ 8.79 (s, 1H ), 7.56-7.53 (m,2H...
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Abstract
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