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Method for synthesizing 6-sulfurylmethylphenanthridine derivatives through visible light catalysis

A technology for sulfomephridine and derivatives, which is applied in the field of visible light catalyzed synthesis of 6-sulfomephridine derivatives, can solve the problems of large functional group limitations, residual metal ions, complicated operation procedures, etc., and achieves the reaction time. Short, low production cost, the effect of simplifying the process flow

Active Publication Date: 2019-01-18
SHANGRAO NORMAL UNIV
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  • Description
  • Claims
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Problems solved by technology

However, the above synthetic methods often have some disadvantages in varying degrees: high reaction temperature, use of expensive metals, high toxicity of individual reagents, serious environmental pollution, low reaction yield; The introduced functional groups are more limited
However, in this method, the more expensive transition metal Ru is used as the photocatalyst, resulting in the residue of metal ions in the product, and the sulfonyl chloride with pungent odor and easier hydrolysis is used as the sulfonylation reagent, and the reaction solvent needs anhydrous treatment, resulting in The operation process is complicated and the cost is high, which limits its application in actual production

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  • Method for synthesizing 6-sulfurylmethylphenanthridine derivatives through visible light catalysis
  • Method for synthesizing 6-sulfurylmethylphenanthridine derivatives through visible light catalysis
  • Method for synthesizing 6-sulfurylmethylphenanthridine derivatives through visible light catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] At room temperature, add magneton, 2-(1-azidovinyl)-1,1'-biphenyl (0.26mmol, 57.5mg), p-toluenesulfonyl hydrazide (0.2mmol, 37.2mg ), Rose Bengal (0.004mmol, 4.07mg), TBPB (0.4mmol, 77.6mg) and Na 2 CO 3 (0.24mmol, 25.44mg), after changing the argon three times under vacuum, add 2ml of acetonitrile, react under 3W blue light irradiation for 10h, after the reaction is over, evaporate the solvent to obtain the crude product, then separate and purify by column chromatography to obtain the present embodiment 6- The product of sulfonemethylphenanthidine was 63.1 mg, the yield was 91%, and it was a pale yellow solid. 1 H NMR (400MHz, CDCl 3 )δ8.64(d,J=8.3Hz,1H), 8.60–8.50(m,1H),8.36(d,J=8.2Hz,1H),7.84(ddd,J=9.8,6.0,4.9Hz,2H ),7.74(t,J=7.6Hz,1H),7.67(dd,J=6.2,3.4Hz,2H),7.56(d,J=8.2Hz,2H),7.18(d,J=8.0Hz,2H ),5.15(s, 2H), 2.38(s,3H). 13 C NMR (101MHz, CDCl 3 )δ149.76,144.61,143.25,135.54,133.78,133.16, 133.10,130.85,129.86,129.39,128.64,127.59,127.58,126.98,125...

Embodiment 2

[0032]

[0033] At room temperature, add magneton, 2-(1-azidovinyl)-4'-methyl-1,1'-biphenyl (0.26mmol, 61.1mg), p-toluenesulfonyl hydrazide (0.2mmol, 37.2mg), Rose Bengal (0.004mmol, 4.07mg), TBPB (0.4mmol, 77.6mg) and Na 2 CO 3 (0.24mmol, 25.44mg), after changing the argon three times under vacuum, add 2ml of acetonitrile, react under 3W blue light irradiation for 10h, after the reaction is over, evaporate the solvent to obtain the crude product, then separate and purify by column chromatography to obtain the present embodiment 6- The product of sulfonemethylphenanthidine was 66.5 mg, the yield was 92%, and it was a pale yellow solid. 1 H NMR (400MHz, CDCl 3 )δ8.56(d, J=8.3Hz, 1H), 8.40(d, J=8.4Hz, 1H), 8.29(d, J=8.2Hz, 1H), 7.85–7.76(m, 1H), 7.71– 7.61(m, 2H), 7.56(d, J=8.3Hz, 2H), 7.47(dd, J=8.4, 1.5Hz, 1H), 7.17(d, J=8.0Hz, 1H), 5.12(s, 2H ), 2.53(s,3H),2.37(s,3H). 13 C NMR (101MHz, CDCl 3 )δ149.65, 144.59, 143.45, 138.83, 135.67, 133.18, 130.76, 129.43, 129.38, 1...

Embodiment 3

[0035]

[0036] At room temperature, add magneton, 2-(1-azidovinyl)-4'-methoxy-1,1'-biphenyl (0.26mmol, 65.3mg), p-toluenesulfonyl Hydrazine (0.2mmol, 37.2mg), Rose Bengal (0.004mmol, 4.07mg), TBPB (0.4mmol, 77.6mg) and Na 2 CO 3 (0.24mmol, 25.44mg), after changing the argon three times under vacuum, add 2ml of acetonitrile, react under 3W blue light irradiation for 10h, after the reaction is over, evaporate the solvent to obtain the crude product, then separate and purify by column chromatography to obtain the present embodiment 6- The product of sulfonemethylphenanthidine was 65.6 mg, the yield was 87%, and it was a pale yellow solid. 1 H NMR (400MHz, DMSO) δ8.71 (d, J = 7.6Hz, 1H), 8.65 (d, J = 8.5Hz, 1H), 8.38 (d, J = 7.5Hz, 1H), 7.88 (s, 1H ),7.64(d,J=6.9Hz, 3H),7.35(d,J=6.9Hz,3H),7.26(s,1H),5.38(s,2H),3.90(s,3H),2.37(s ,3H). 13 C NMR(101 MHz,DMSO)δ160.20,151.10,144.96,144.82,136.74,133.17,131.58,130.00,128.65,128.06, 126.87,124.80,124.43,122.41,118.75,117.95,109.9...

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Abstract

The invention relates to a method for synthesizing 6-sulfurylmethylphenanthridine derivatives through visible light catalysis. Sulfonyl chloride is replaced with stable sulfohydrazide to be used as sulfonylation reagents; organic dye rose-bengal is used as a photocatalyst; under the oxidizing agents, alkali and illumination conditions, the vinyl azide serial connection sulfonylation reaction is realized; the 6-sulfurylmethylphenanthridine derivatives are synthesized. Compared with the existing method, the method has the characteristics that the reaction conditions are mild; a nonmetal photocatalyst is used; the stable and easy-to-obtain benzenesulfonylhydrazine is used as the sulfonylation reagent; the substrate application range is wide; the atom economic performance is high; the environmental-friendly effect is good; the step economic performance is good, and the like.

Description

technical field [0001] A method for synthesizing 6-sulfonemethylphenanthridine derivatives by visible light catalysis of the present invention involves the use of stable and easily available sulfonyl hydrazide as a sulfonylation reagent and the organic dye rose bengal as a photocatalyst under the condition of visible light irradiation. The invention relates to a series cyclization reaction of an alkenyl azide compound, a step-by-step construction of a C-S bond and a C-N bond, and a method for synthesizing 6-sulfonemethylphenanthidine derivatives, specifically belonging to the technical field of organic synthesis. Background technique [0002] Pyridine skeleton molecules widely exist in various pharmaceutical intermediates, natural products and functional materials, and are the synthetic building blocks of various complex and valuable organic compounds. In particular, phenanthridine and its derivatives have attracted extensive attention from chemists due to their unique photo...

Claims

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Application Information

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IPC IPC(8): C07D221/12C07D409/12
CPCC07D221/12C07D409/12
Inventor 毛刘量全丽霞周安西朱志鹏祝显虹
Owner SHANGRAO NORMAL UNIV
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