A photocatalytic synthesis method of C2 substituted 2h-benzothiazole hydroxyalkylated derivatives
A technology of benzothiazole hydroxyalkyl and synthesis method, which is applied in the field of photocatalytic synthesis of C2-substituted 2H-benzothiazole hydroxyalkylated derivatives, can solve the problems of residues, toxic metals, high price and the like, and achieves a catalytic system Simple, mild reaction conditions, and broad substrate effect
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Embodiment 1
[0022] Example 1 Derivative Ia((R)n=H, R 1 =H,R 2 = methyl) synthesis
[0023] Weigh 2H-benzothiazole (0.3mmol, 40.6mg), ethanol (6.0mmol, 276.4mg), Selectfluor (0.9mmol, 318.9mg) and trifluoroacetic acid (0.30mmol, 34.2mg) in a 25mL reaction tube, and then Add acetonitrile (58mmol, 2.4g), place it under the irradiation of a 20W LED blue light to react, stir the reaction at room temperature, and monitor it by TLC. After about 16h, the reaction ends, the reaction solution is concentrated to remove the solvent, and the concentrate is separated by column chromatography (washing The solvent removal is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:1) to obtain a yellow solid, namely the derivative Ia. Yield 71%.
[0024] of the compound 1 H NMR and 13 C NMR analysis data are described below,
[0025] 1 H NMR (500MHz, CDCl 3 )δ7.96(d, J=8.0Hz, 1H), 7.86(d, J=8.0Hz, 1H), 7.45(dd, J=8.0, 7.0Hz, 1H), 7.36(t, J=8.0Hz, 1H), 5.25(q, J=6.5Hz, 1H), 3.81(br, 1...
Embodiment 2
[0026] Example 2 Derivative Ib((R)n=H, R 1 =H,R 2 = ethyl) synthesis
[0027]Weigh 2H-benzothiazole (0.3mmol, 40.6mg), n-propanol (6.0mmol, 360.6mg), Selectfluor (0.9mmol, 318.9mg) and trifluoroacetic acid (0.30mmol, 34.2mg) in a 25mL reaction tube , then add acetonitrile (65mmol, 2.7g), place it under the irradiation of 20W LED blue light to react, stir the reaction at room temperature, TLC monitoring, after about 18h, the reaction ends, the reaction solution is concentrated to remove the solvent, and the concentrate is separated by column chromatography (The eluent is a mixed solvent of petroleum ether-ethyl acetate with a volume ratio of 1:1) to obtain a white solid, namely derivative Ib. Yield 60%.
[0028] of the compound 1 H NMR and 13 C NMR analysis data are described below,
[0029] 1 H NMR (500MHz, CDCl 3 )δ7.98(d,J=8.5Hz,1H),7.88(d,J=8.0Hz,1H),7.50–7.44(m,1H),7.41–7.35(m,1H),5.05(dd,J =7.5,5.0Hz,1H),3.70(br,1H),2.09(m,1H),2.01–1.93(m,1H),1.07(t,J=7.5Hz,3H). ...
Embodiment 3
[0030] Example 3 Derivatives Ic((R)n=H, R 1 = methyl, R 2 = methyl) synthesis
[0031] Weigh 2H-benzothiazole (0.3mmol, 40.6mg), isopropanol (6.0mmol, 360.6mg), Selectfluor (0.6mmol, 212.6mg) and trifluoroacetic acid (0.30mmol, 34.2mg) in a 25mL reaction tube , add acetonitrile (58mmol, 2.4g) again, place reaction under 20WLED blue light lamp, stir reaction at room temperature, TLC monitors, after about 16h, reaction finishes, and reaction solution is concentrated to remove solvent, and concentrated solution is separated through column chromatography (eluent (Petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:1) to obtain a white solid, namely the derivative Ic. Yield 85%.
[0032] of the compound 1 H NMR and 13 C NMR analysis data are described below,
[0033] 1 H NMR (500MHz, CDCl 3 )δ8.00(d, J=8.0Hz, 1H), 7.89(d, J=8.0Hz, 1H), 7.48(t, J=7.5Hz, 1H), 7.38(t, J=7.0Hz, 1H) ,3.35(br,1H),1.77(s,6H). 13 C NMR (125MHz, CDCl 3 )δ180.10, 153.05, 135.30, 1...
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