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Visible light preparation method for azatraasterane compounds

A technology of azatetrastartane and visible light, which is applied in organic chemistry and other fields, and can solve the problems of many by-products, low wavelength selectivity, and short service life.

Inactive Publication Date: 2020-07-03
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The light source used in this synthesis process has low wavelength selectivity and difficult control of reaction temperature, which leads to low selectivity of photochemical reaction, many by-products, difficult separation of target products and low synthesis yield, high energy consumption and short service life of the light source, etc. Shortcomings seriously affect the synthesis and application research of azatetrasterane compounds

Method used

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  • Visible light preparation method for azatraasterane compounds
  • Visible light preparation method for azatraasterane compounds
  • Visible light preparation method for azatraasterane compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Weigh 2.91g (10mmol) of ethyl 1,4-diphenyl-1,4-dihydropyridine-3-carboxylate and 0.23g (0.5mmol) of visible light catalyst Flavin into a round bottom flask, dissolve in 20ml tetrahydrofuran In a mixed solvent with methanol (V:V=1:1), under nitrogen protection, the resulting reaction solution was irradiated at room temperature under a 50W white light energy-saving lamp light source, and the light source was 20cm away from the reactant. The reaction was tracked by TLC. After the reaction was complete, the target product 3,6,9,12-tetraphenyl-7,11-dicarboxylic acid ethyl ester-3,9-diazatetrapentane could be obtained by direct filtration.

[0022]

[0023] 1 H NMR (400MHz, CDCl 3 )δ H (ppm):7.34-6.88(m,20H),5.33(d,2H),4.95(d,2H),4.20-4.04(m,4H),3.73(d,2H),3.53(td,2H), 1.10(t,6H); 13 C NMR (100MHz, CDCl 3 )δ C (ppm):174.56,150.58,140.65,129.35,128.97,128.05,126.18,119.44,116.85,60.94,55.87,53.87,53.69,40.76,38.62,13.97.HRMS(ESI + )m / z[M+H] + C 40 h 39 N 2 o 4 T...

Embodiment 2

[0025] Weigh 2.91g (10mmol) of ethyl 1,4-diphenyl-1,4-dihydropyridine-3-carboxylate and 0.55g (0.7mmol) of visible light catalyst 4CzTPN into a round bottom flask, dissolve in 20ml THF In a mixed solvent with methanol (V:V=1:1), under nitrogen protection, the resulting reaction solution was irradiated under a 10W blue LED light source at room temperature, and the light source was 20 cm away from the reactant. The reaction was tracked by TLC. After the reaction was complete, the target product 3,6,9,12-tetraphenyl-7,11-dicarboxylic acid ethyl ester-3,6-diazatetrapentane could be obtained by direct filtration.

[0026]

[0027] 1 H NMR (400MHz, CDCl 3 )δ H (ppm):7.31-6.88(m,20H),5.30(d,2H),4.59-4.54(d,2H),4.35(d,2H),4.21-4.08(m,4H),3.37(d,2H ), 1.10(t, 6H); 13C NMR (100MHz, CDCl 3 )δ C (ppm): 174.55, 149.74, 141.27, 129.06, 128.77, 128.15, 125.76, 119.90, 116.31, 61.23, 55.60, 50.79, 49.65, 44.10, 39.53, 14.02. HRMS (ESI + )m / z[M+H] + C 40 h 39 N 2 o 4 The theoreti...

Embodiment 3

[0029] Weigh 3.24g (10mmol) of ethyl 1-(4-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.32g (0.5mmol) of visible light catalyst Eosin Y into a round bottom flask , dissolved in 20ml of ethanol solvent, under nitrogen protection, and placed the resulting reaction solution at room temperature under a 50W white light energy-saving lamp light source, and the light source was 20cm away from the reactant. TLC followed the reaction. After the reaction was complete, directly filter to obtain the target product 3,9-(4-bromophenyl)-1,5,7,11-ethyl tetracarboxylate-3,9-diazatetrastar alkyl.

[0030]

[0031] 1 H NMR (400MHz, CDCl 3 )δ H (ppm):7.01-7.24(m,12H),6.62(d,4H),4.83(m,4H),4.16(d,6H),2.21(s,2H),1.96(d,4H),1.21( d,4H); 13 C NMR (100MHz, CDCl 3 )δ C (ppm): 177.9, 148.6, 132.5, 116.5, 116.2, 71.8, 61.9, 47.6, 38.9, 14.1. HRMS (ESI + )m / z[M+H] + C 34 h 36 Br 2 N 2 o 8 The theoretical calculation value is 760.4852, and the detection value is 760.4856.

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Abstract

The invention discloses a visible light preparation method for azatraasterane compounds, belonging to the technical field of synthesis of organic compounds. According to the azatraasterane provided bythe invention, at least one selected from X in a ring 1 and X in a ring 2 is a nitrogen atom, and the other X is a carbon atom. The method comprises the following steps: with a 1,4-dihydropyridine derivative or / and a 1,4-dihydropyrazine derivative as a reaction substrate, dissolving the reaction substrate and a visible light catalyst in a solvent, and carrying out [2+2] photocyclization reactionunder the irradiation of visible light. The method has the advantages of simple synthetic route, simple and convenient operation, high chemical selectivity, high yield, environment friendliness, conservation of energy, cleanness and the like.

Description

technical field [0001] The invention relates to a visible light preparation method of azatetrastartane compounds, belonging to the technical field of organic compound synthesis. Background technique [0002] Azatetrasterane compounds are derivatives of polyhedral alkanes. Due to the particularity of their cage structure, they have physical and chemical properties different from other organic compounds, and exhibit good physiological and pharmacological activities such as antiviral and antitumor. . The key synthesis step of azatetrastarane compounds is the [2+2] photocyclization reaction, that is, under the action of light, two olefin molecules undergo a cyclization reaction to generate cyclobutane derivatives. The synthesis method of azatetrastarane compounds reported in the literature is mainly to undergo intermolecular or intramolecular [2+2] photocyclization reaction of nitrogen-containing cyclohexadiene compounds under the irradiation of ultraviolet lamps. The light so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 闫红孙润之张晓坤王琰宇崔景瑞
Owner BEIJING UNIV OF TECH
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