Axial chiral benzopyrazine compound as well as preparation method and application thereof
A technology for aniline compounds and benzopyrazines is applied in the field of axial chiral benzopyrazine compounds and their preparation, and achieves the effects of low equipment requirements, high yield and high stereoselectivity
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[0035] Another aspect of the embodiments of the present invention also provides a method for preparing a class of axial chiral benzopyrazine compounds, comprising:
[0036] The mixed reaction system comprising the ortho-substituted aniline compound, the dicarbonyl compound, the reaction assistant and the solvent is reacted at -20 to 25° C. for 8-12 hours to obtain the axial chiral benzopyrazine compound.
[0037]In some specific embodiments, the ortho-substituted aniline compounds include 2-(8-methoxy-2,4-dimethyl-1H-pyrrol-1-yl)aniline, 2-(2, 4-Dimethyl-1H-pyrrol-1-yl)aniline, 2-(8-benzyloxy-2,4-dimethyl-1H-pyrrol-1-yl)aniline, 2-(8-fluoro- 2,4-Dimethyl-1H-pyrrol-1-yl)aniline, 2-(8-bromo-2,4-dimethyl-1H-pyrrol-1-yl)aniline, 2-(7-(N , N-dimethyl)2,4-dimethyl-1H-pyrrol-1-yl)aniline, any one or a combination of two or more, but not limited thereto.
[0038] In some more specific embodiments, the dicarbonyl compounds include 2-methoxy-1-naphthaldehyde, 2,7-dimethoxy-1-naphthald...
Embodiment 1
[0055] Weigh 0.6mmol of 2-(8-methoxy-2,4-dimethyl-1H-pyrrol-1-yl)aniline and 0.5mmol (2.0%) of chiral phosphoric acid A3 into the reaction flask, then Mix with 5ml of mixed solvent of p-xylene and toluene (volume ratio is 2:1), then add 2-methoxy-1-naphthalenecarboxaldehyde at 0°C, and react at this temperature for 12h, and then use vacuum to reduce pressure The reaction solvent was removed by the method of , and the final product was purified by column chromatography, (S)-4-(2-methoxynaphthalene-1-)-1,3-dimethyl-4,5-dihydro Pyrro[1,2-α]quinoxaline, yellow solid, 68.7 mg, yield: 98%, chiral purity: 92% ee.
[0056] Characterization test of (S)-4-(2-methoxynaphthalene-1-)-1,3-dimethyl-4,5-dihydropyrro[1,2-α]quinoxaline obtained above :
[0057] 1 The characterization data of H-NMR are: (400MHz, Chloroform-d)δ8.8-8.5(m,1H),8.0-7.8(m,2H),7.6(d,J=8.0Hz,1H),7.5-7.3 (m, 3H), 7.0 (dt, J=31.0, 7.5Hz, 2H), 6.8–6.6 (m, 2H), 5.8 (s, 1H), 4.0 (d, J=43.5Hz, 4H), 2.7 ( s, 3H), 1.2(s, 3...
Embodiment 2
[0068] Weigh 0.6 mmol of 2-(2,4-dimethyl-1H-pyrrole)-4-methoxyaniline and 0.5 mmol (2.0%) of chiral phosphoric acid A3 into the reaction flask, and then mix with 5 ml of solvent tetrahydrofuran. Mixed, then added 2-methoxy-1-naphthalene carboxaldehyde at -20 ° C, and reacted at this temperature for 8 h, then removed the reaction solvent by vacuum decompression, and purified by chromatographic column chromatography to obtain the final product , (S)-8-methoxy-4-(2-methoxynaphthalene-1-)-1,3-dimethyl-4,5-dihydropyrro[1,2-α]quinoxaline , yellow solid, 75.3 mg, yield: 98%, chiral purity: 92% ee.
[0069] (S)-8-methoxy-4-(2-methoxynaphthalene-1-)-1,3-dimethyl-4,5-dihydropyrrole[1,2-α] obtained above Characterization of quinoxaline:
[0070] 1 The characterization data of H-NMR are: (400MHz, Chloroform-d) δ8.5–8.4 (m, 1H), 7.8 (d, J=9.0Hz, 1H), 7.8–7.7 (m, 1H), 7.3–7.2 (m,3H),7.2(d,J=2.6Hz,1H),6.6(d,J=8.5Hz,1H),6.5(dd,J=8.5,2.6Hz,1H),6.4(s,1H) , 5.7(s, 1H), 3.9(s, 3H), 3.8(s, 4H...
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