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Method for synthesizing 11-sulfenylnaphtho[2,3-b]benzofuran compound

A technology of benzofuran and 3-b, which is applied in the field of synthesizing 11-thionaphtho[2,3-b]benzofuran compounds, can solve the problem of low tolerance of substrate functional groups and achieve considerable yield , High industrial practical value, easy operation

Active Publication Date: 2021-03-05
GUILIN MEDICAL UNIVERSITY
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Problems solved by technology

The traditional synthesis of dibenzofuran mainly has the following two methods: synthesis by intramolecular oxidative cyclization of 2-arylphenol (J.Am.Chem.Soc.2011,133,9250.); transition metal-promoted 1-benzene Intramolecular cyclization reaction synthesis of oxy-2-nitrobenzene and 2-phenoxybenzoic acid ((a) Org. Lett. 2019, 21, 4721; (b) Org. Lett. 2013, 15, 2754. ), there are limitations such as the use of transition metals in the above methods, and the low tolerance of substrate functional groups. Therefore, it is highly desirable to develop efficient and green synthetic methods. Potential pharmacological activity (J.Med.Chem.2006,49,3172.), the development of efficient synthesis of thioheterocyclic compounds has been a research hotspot

Method used

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  • Method for synthesizing 11-sulfenylnaphtho[2,3-b]benzofuran compound
  • Method for synthesizing 11-sulfenylnaphtho[2,3-b]benzofuran compound
  • Method for synthesizing 11-sulfenylnaphtho[2,3-b]benzofuran compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation and characterization of 11-(phenylthio)naphtho[2,3-b]benzofuran:

[0022]

[0023] Add 0.2 mmol of 1-phenylethynyl-2-vinyloxybenzene, 0.3 mmol of benzenethiobenzenesulfonate, 50 mol% of diphenyl disulfide, 5 mol% of eosin disodium salt, and 2 mL of acetonitrile into a quartz tube , set the temperature at 90°C, stirred and reacted for 12h under nitrogen and 30W white light irradiation, after the reaction was completed, the mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography with petroleum ether to obtain a white solid product with a yield of 70 %.

[0024] The product is characterized by:

[0025] 1 H NMR (400MHz, CDCl 3 )δ8.68(t,J=7.5Hz,2H),8.01–7.94(m,2H),7.49(ddd,J=15.3,9.8,5.1Hz,4H),7.27(dd,J=10.8,4.1Hz ,1H),7.10–6.98(m,5H). 13 C NMR (100MHz, CDCl 3 ( M] + calcd for C 22 h 14 OS, 326.0765; found, 326.0763.

Embodiment 2

[0027] Preparation and characterization of 8-bromo-11-(phenylthio)naphtho[2,3-b]benzofuran:

[0028]

[0029] Add 0.2mmol of 1-(4-bromophenyl)ethynyl-2-vinyloxybenzene, 0.3mmol of benzenethiobenzenesulfonate, 50mol% of diphenyl disulfide, and eosin disodium salt into the quartz tube 5mol%, acetonitrile 2mL, set the temperature at 90°C, stirred and reacted for 12h under nitrogen and 30W white light irradiation, after the reaction was completed, the mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography with petroleum ether to obtain a white solid product , the yield was 58%.

[0030] The product is characterized by:

[0031] 1 H NMR (400MHz, CDCl 3 )δ8.56–8.51(m,1H),8.41(d,J=9.1Hz,1H),7.98(d,J=1.9Hz,1H),7.74(s,1H),7.44–7.38(m,3H ),7.18(ddd,J=8.1,6.3,2.0Hz,1H),7.03–6.98(m,2H),6.92(ddd,J=13.2,6.9,4.2Hz,3H). 13 C NMR (100MHz, CDCl 3 ( M] + calcd for C 22 h 13 BrOS, 405.9850; found, 405.9858.

Embodiment 3

[0033] Preparation and product characterization of 8-methyl-11-(phenylthio)naphthalene[2,3-b]benzofuran:

[0034]

[0035] Add 0.2mmol of 1-(p-tolylethynyl)-2-vinyloxybenzene, 0.3mmol of benzenethiobenzenesulfonate, 50mol% of diphenyl disulfide, 5mol% of eosin disodium salt, Acetonitrile 2mL, set the temperature at 90°C, stirred and reacted for 12h under nitrogen and 30W white light irradiation, after the reaction was completed, the mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography with petroleum ether to obtain a white solid product, the yield 65%.

[0036] The product is characterized by:

[0037] 1 H NMR (400MHz, CDCl 3 )δ8.63(s,1H),8.56(d,J=8.8Hz,1H),7.88(s,1H),7.71(s,1H),7.51(d,J=8.1Hz,1H),7.48– 7.42(m,1H),7.32–7.20(m,3H),7.08(dd,J=10.4,4.4Hz,2H),7.02(d,J=7.3Hz,2H),2.50(s,3H). 13 C NMR (100MHz, CDCl 3 )δ157.9, 154.4, 137.5, 136.2, 133.7, 131.0, 129.5, 129.1, 128.8, 128.1, 127.2, 126.5, 125.8, 125.3, 124.9...

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Abstract

The invention discloses a method for synthesizing a 11-sulfenylnaphtho[2,3-b]benzofuran compound. The method is characterized in that 2-ethyleneoxyphenylacetylene and thiosulfonate are used as substrates, disulfide is used as an additive, Na2-Eosin Y is used as a photosensitizer, and light-irradiation stirring is performed under inert gas and heating conditions to obtain the product 11-sulfenylnaphtho[2,3-b]benzofuran. The method has the advantages of no need for transition metal addition in reactions, simple operation, considerable yield, environmental protection performance and good application prospects.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 11-thionaphtho[2,3-b]benzofuran compounds. Background technique [0002] The dibenzofuran skeleton widely exists in natural products and drug molecules, and has a variety of biological activities, so its synthesis method has attracted extensive attention. The traditional synthesis of dibenzofuran mainly has the following two methods: synthesis by intramolecular oxidative cyclization of 2-arylphenol (J.Am.Chem.Soc.2011,133,9250.); transition metal-promoted 1-benzene Intramolecular cyclization reaction synthesis of oxy-2-nitrobenzene and 2-phenoxybenzoic acid ((a) Org. Lett. 2019, 21, 4721; (b) Org. Lett. 2013, 15, 2754. ), there are limitations such as the use of transition metals in the above methods, and the low tolerance of substrate functional groups. Therefore, it is highly desirable to develop efficient and green synthetic methods. Potential pharm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/77
CPCC07D307/77
Inventor 陈艳艳徐燕丽陈慧
Owner GUILIN MEDICAL UNIVERSITY
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