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Method for performing cyclized synthesis on multi-substituted indole through elemental iodine promoted enaminone

A technology of enaminone and elemental iodine is applied in the field of cyclization of enaminones promoted by elemental iodine to synthesize polysubstituted indole, and achieves the effects of high product yield, high atom economy, wide biological activity and medicinal value

Active Publication Date: 2018-06-22
SHAANXI NORMAL UNIV
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AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of existing indole compound synthesis methods, and provide a method for synthesizing multi-substituted indoles with no transition metal catalysis, no need to add ligands, simple operation, single reaction product, and high efficiency

Method used

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  • Method for performing cyclized synthesis on multi-substituted indole through elemental iodine promoted enaminone
  • Method for performing cyclized synthesis on multi-substituted indole through elemental iodine promoted enaminone
  • Method for performing cyclized synthesis on multi-substituted indole through elemental iodine promoted enaminone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of 5-methoxy-2-phenyl-3-benzoylindole of the following structural formula

[0017]

[0018] Add 0.1647g (0.5mmol) (Z)-3-(4-methoxyanilino)-1,3-diphenyl-2-en-1-one, 0.1520g (0.6mmol ) elemental iodine, 0.2879g (1.5mmol) cesium acetate, 4mL 1,4-dioxane, stirred and reacted at 80°C for 24 hours, stopped the reaction, cooled down to room temperature naturally, and separated with a silica gel column (the eluent was ethyl acetate ester and petroleum ether volume ratio of 1:5 mixture), to obtain 5-methoxy-2-phenyl-3-benzoyl indole, and its yield was 94%.

[0019] The resulting product was characterized by a Bruker Avance superconducting Fourier digital NMR spectrometer, and the characterization data were: 1 H NMR (600MHz, DMSO) δ12.10 (s, 1H), 7.50 (d, J = 7.2Hz, 2H), 7.42 (d, J = 8.7Hz, 1H), 7.34 (dd, J = 15.5, 7.8Hz ,4H),7.26-7.15(m,5H),6.91(dd,J=8.7,2.4Hz,1H),3.74(s,3H); 13 C NMR (151MHz, DMSO) δ192.03, 155.12, 144.62, 139.97, 131.70, 131.05, 130.84, 129.4...

Embodiment 2

[0027] Preparation of 5-methoxy-2-phenyl-3-(4-methylbenzoyl) indole of the following structural formula

[0028]

[0029] In Example 1, the (Z)-3-(4-methoxyanilino)-1,3-diphenyl-2-en-1-one used was equimolar with (Z)-3-( 4-methoxyanilino)-3-phenyl-1-(4-methylphenyl)-2-en-1-one is replaced, and other steps are the same as in Example 1 to obtain 5-methoxy-2 -Phenyl-3-(4-methylbenzoyl)indole in 98% yield.

[0030] The resulting product was characterized by a Bruker Avance superconducting Fourier digital NMR spectrometer, and the characterization data were: 1 H NMR (600MHz, CDCl 3 )δ8.98(s,1H),7.43(d,J=8.0Hz,2H),7.37(d,J=2.1Hz,1H),7.23-7.14(m,3H),7.06(t,J=7.3 Hz,1H),7.01(t,J=7.3Hz,2H),6.84(d,J=7.9Hz,2H),6.80(dd,J=8.8,2.4Hz,1H),3.69(s,3H), 2.17(s,3H); 13 C NMR (151 MHz, CDCl 3 )δ 193.41, 155.85, 144.08, 142.09, 136.98, 131.86, 130.65, 129.87, 129.49, 129.15, 128.41, 128.23, 113.96, 113.61, 112.01, 102.92, 55.72, 21.48

Embodiment 3

[0032] Preparation of 5-methoxy-2-phenyl-3-(4-nitrobenzoyl) indole of the following structural formula

[0033]

[0034] In Example 1, the (Z)-3-(4-methoxyanilino)-1,3-diphenyl-2-en-1-one used was equimolar with (Z)-3-( 4-methoxyanilino)-3-phenyl-1-(4-nitrophenyl)-2-en-1-one is replaced, and other steps are the same as in Example 1 to obtain 5-methoxy-2 -Phenyl-3-(4-nitrobenzoyl)indole in 97% yield.

[0035] The resulting product was characterized by a Bruker Avance superconducting Fourier digital NMR spectrometer, and the characterization data were: 1 H NMR (600MHz, DMSO) δ12.28(s, 1H), 7.93(d, J=8.7Hz, 2H), 7.61(d, J=8.7Hz, 2H), 7.57(d, J=2.4Hz, 1H ), 7.43(d, J=8.8Hz, 1H), 7.32-7.26(m, 2H), 7.22(t, J=7.3Hz, 1H), 7.17(t, J=7.3Hz, 2H), 6.94(dd ,J=8.8,2.5Hz,1H),3.79(s,3H); 13 C NMR(151MHz,DMSO)δ190.08,155.65,147.99,146.42,146.00,131.30,130.81,129.94,129.91,128.71,128.62,127.86,122.61,113.18,115.77,111.28,

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Abstract

The invention discloses a method for performing cyclized synthesis on multi-substituted indole through elemental-iodine promoted enaminone. The method comprises a step of performing intramolecular cyclization on the enaminone under conditions that low-cost and low-toxicity elemental iodine is used as a promoting agent and cesium acetate is alkali so as to generate the multi-substituted indole. According to the method disclosed by the invention, the use of a transitional metal catalyst is not needed, and addition of ligands is not needed, so that an operation is simple, a reaction product is single, and the atomic economy is high; and moreover, the product is only subjected to simple column chromatographic separation after the reaction is carried out, so that the yield of the product is high, and the obtained multi-substituted indole has wide biological activity and has a medicinal value.

Description

technical field [0001] The invention belongs to the technical field of polysubstituted indole synthesis, and in particular relates to a method for synthesizing polysubstituted indole by enaminone cyclization promoted by elemental iodine. Background technique [0002] Indole and its derivatives are an important class of heterocyclic fine chemical raw materials, which are widely used in the fields of medicine, pesticides, spices, dyes, and food and feed additives. The research on its application has been persistent, and new application fields are still emerging. are constantly being developed. [0003] Fisher's indole synthesis method remains one of the most efficient to date. However, its shortcomings are also evident in today's push for sustainable chemistry. Chemists are working on the application of oxidative coupling strategies to study new reactions for the synthesis of indoles, but most of these new methods require the use of expensive transition metal catalysts such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
Inventor 高子伟苏洁张伟强庄梦媛马富余孙华明
Owner SHAANXI NORMAL UNIV
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