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Preparation method of indolizine cyclo-1, 2-diketone with fluorescence activity and derivative thereof

A technology of indolezine and phenylindolezine, which is applied in the field of preparation of indolezine ring-1,2-dione and its derivatives, and can solve the problems of harsh conditions, narrow scope of application of substrates, low yield, etc. problems, to achieve the effect of easy operation, wide application range and simple operation

Active Publication Date: 2020-06-12
山东中新科农生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a quick and convenient method with mild conditions to prepare a class of fluorescently active indoleazine ring-1,2-dione and its derivatives to solve the problem of synthesizing indoleazines in the prior art. The disadvantages of cyclo-1,2-dione are harsh conditions, narrow scope of substrate application and low yield

Method used

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  • Preparation method of indolizine cyclo-1, 2-diketone with fluorescence activity and derivative thereof
  • Preparation method of indolizine cyclo-1, 2-diketone with fluorescence activity and derivative thereof
  • Preparation method of indolizine cyclo-1, 2-diketone with fluorescence activity and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Sample preparation and testing:

[0043] Put 19.3mg (0.1mmol) of 2-phenylindolezine and 1.1mg (0.001mmol) of Rose Bengal into a 25ml test tube with a stirring bar, add 1mL of dimethyl sulfoxide at room temperature, and then add 20.1 mg (0.15 mmol) of 2-oxo-2-phenylacetaldehyde, stirred for 12 hours under blue light irradiation, spin-dried and flash column chromatography to obtain the target product.

[0044]

[0045] Result analysis:

[0046] (1) Proton NMR spectrum: 1 H NMR (400MHz, Chloroform-d) δppm10.09(d, J=6.9Hz, 1H), 7.67-7.62(m, 2H), 7.59(d, J=8.7Hz, 1H), 7.50(t, J= 7.3Hz, 1H), 7.33(q, J=8.7, 8.0Hz, 3H), 7.14(d, J=7.3Hz, 1H), 7.07(t, J=8.7Hz, 3H), 7.00(t, J= 7.5Hz,2H),6.53(s,1H).

[0047] (2) Carbon NMR spectrum: 13 C NMR (100MHz, Chloroform-d) δppm 192.4, 183.2, 142.2, 139.4, 134.2, 134.0, 133.6, 130.4, 129.6, 129.6, 128.4, 128.0, 127.6, 126.6, 118.8, 118.5, 114.9, 106.

[0048] (3) High resolution mass spectrometry: HRMS MALDI (m / z): calcd for C 22 h...

Embodiment 2

[0051] Sample preparation and testing:

[0052] Put 14.2mg (0.1mmol) of 1-cyanindolezine and 1.1mg (0.001mmol) of Rose Bengal into a 25ml test tube with a stirring bar, add 1mL of dimethyl sulfoxide at room temperature, and then add 20.1 mg (0.15 mmol) of 2-oxo-2-phenylacetaldehyde, stirred for 12 hours under blue light irradiation, spin-dried and flash column chromatography to obtain the target product.

[0053]

[0054] Result analysis:

[0055] (1) Proton NMR spectrum: 1 H NMR (400MHz, Chloroform-d) δppm 9.95(d, J=7.0Hz, 1H), 8.03(d, J=6.9Hz, 2H), 7.84(d, J=8.8Hz, 1H), 7.75(s, 1H), 7.65(t, J=7.4Hz, 1H), 7.60-7.56(m, 1H), 7.50(t, J=7.7Hz, 2H), 7.26-7.21(m, 1H).

[0056] (2) Carbon NMR spectrum: 13 C NMR (100MHz, Chloroform-d) δppm 191.8, 181.6, 141.8, 134.9, 132.9, 130.3, 130.3, 129.9, 129.3, 129.0, 120.6, 117.8, 117.0, 114.4, 86.9.

[0057] (3) High resolution mass spectrometry: HRMS MALDI (m / z): calcd for C 17 h 10 N 2 o 2 [M+Na] + :297.0635,found:297.0644.

...

Embodiment 3

[0060] Sample preparation and testing:

[0061] Put 19.3mg (0.1mmol) of 2-phenylindolezine and 1.1mg (0.001mmol) of Rose Bengal into a 25ml test tube with a stirring bar, add 1mL of dimethyl sulfoxide at room temperature, and then add 10.8 mg (0.15 mmol) of methylglyoxal, stirred for 12 hours under blue light irradiation, spin-dried and flash column chromatography to obtain the target product.

[0062]

[0063] Result analysis:

[0064] (1) Proton NMR spectrum: 1 H NMR (400MHz, Chloroform-d) δppm 9.84 (d, J = 6.9Hz, 1H), 7.56 (d, J = 8.4Hz, 1H), 7.39 (dd, J = 4.3, 2.2Hz, 3H), 7.36- 7.34(m, 2H), 7.29(d, J=7.4Hz, 1H), 6.97(t, J=6.8Hz, 1H), 6.57(d, J=1.5Hz, 1H), 2.15(s, 3H).

[0065] (2) Carbon NMR spectrum: 13 C NMR (100MHz, Chloroform-d) δppm 200.4, 183.4, 141.6, 139.3, 135.3, 129.9, 129.1, 128.4, 128.3, 126.3, 118.5, 117.2, 114.70, 105.7, 26.3.

[0066] (3) High resolution mass spectrometry: HRMS MALDI (m / z): calcd for C 17 h 13 NO 2 [M+Na] + :286.0839,found:286.08...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of indolizine cyclo-1, 2-diketone with fluorescence activity and a derivative thereof. The indolizine cyclo-1, 2-diketone is prepared by adopting a new metal-free photocatalytic oxidation method, and the indolizine cyclo-1, 2-diketone is synthesized from commercially available indolizine, 2-oxo-2-phenylacetaldehyde, rose bengal and other basic raw materials, wherein the groups R1, R2 and R3 are alkyl, an electron withdrawing group or an electron donating group; rose bengal can also be replaced with a photocatalyst eosin Y, eosin B, rhodamine 6G or fluorescein; the solvent dimethyl sulfoxide can also be replaced with an organic solvent N, N-dimethylformamide, acetonitrile or dichloromethane. The method has the characteristics of easily available starting materials, wide substrate application range, economy, high efficiency, mild conditions, environmental friendliness and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a class of indazine ring-1,2-dione with fluorescence activity and derivatives thereof. Background technique [0002] Indole compounds are very important nitrogen-containing heterocyclic compounds, which are widely used in many fields such as pesticides, medicines, food additives, dyes, etc., and are usually used in the discovery of various small molecules; functionalized indole drug molecules have potential The biological activity of the biological activity widely exists in active organisms, natural products and synthetic drug molecules, and has become the core structural unit of many drug molecules, and has a wide range of applications in medical and clinical research, such as antifungal, anti-inflammatory, Anti-cancer, anti-tumor, anti-oxidant, anti-tuberculosis, antioxidant, phosphatase inhibitors and antagonists; In this case, it plays an anti-inflamm...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1029C09K2211/1088
Inventor 曹华刘想
Owner 山东中新科农生物科技有限公司
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