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Method for preparing functionalized thiazole heterocyclic compounds through Cu (I) catalyzed multi-component cyclization reaction, and applications of functionalized thiazole heterocyclic compounds

A technology for heterocyclic compounds and cyclization reactions, applied in the fields of botany equipment and methods, applications, organic chemistry, etc., can solve the problems of narrow substrate application range and harsh conditions, and achieve simple and easy operation, wide application range, and harvest high rate effect

Active Publication Date: 2020-06-02
GUANGDONG PHARMA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Another object of the present invention is to provide a quick and convenient synthetic method with mild conditions to prepare thiazole molecules by thioamides, so as to solve the harsh conditions and substrates that exist in the preparation of thiazole molecules by thioamides in the prior art. Narrow scope of application, need for multi-step synthesis and other defects

Method used

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  • Method for preparing functionalized thiazole heterocyclic compounds through Cu (I) catalyzed multi-component cyclization reaction, and applications of functionalized thiazole heterocyclic compounds
  • Method for preparing functionalized thiazole heterocyclic compounds through Cu (I) catalyzed multi-component cyclization reaction, and applications of functionalized thiazole heterocyclic compounds
  • Method for preparing functionalized thiazole heterocyclic compounds through Cu (I) catalyzed multi-component cyclization reaction, and applications of functionalized thiazole heterocyclic compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 41.2mg (0.3mmol) thioamide and 58.5mg (0.45mmol) alkyne aldehyde into a 10mL reaction flask with a stirring bar, add 3mL (0.033M) methanol at room temperature, and then add 14.0mg (0.015mmol) catalyst CuBr (PPh 3 ) 3 and 30.6 mg (0.3 mmol) of pivalic acid, stirred at 60° C. for 8 hours, spin-dried and separated by silica gel chromatography to obtain the target product with a yield of 79%.

[0028]

[0029] Thiazole Heterocyclic Compounds 1 H NMR, 13 C NMR, HR-ESI-MS spectrogram data are as follows:

[0030] 1 H NMR (400MHz, CDCl 3 ): δ7.89(d, J=3.5Hz, 2H), 7.59(s, 1H), 7.45-7.37(m, 8H), 5.51(s, 1H), 3.42(s, 3H).

[0031] 13 C NMR (101MHz, CDCl 3 ): δ169.3, 150.0, 141.2, 140.5, 133.5, 133.1, 131.6, 130.3, 129.3, 129.2, 129.1, 128.9, 128.5, 127.2, 127.1, 126.8, 126.5, 79.5, 57.1.

[0032] HR-MALDI-MS: m / z calcd.for C 17 h 15 NOS[M+H] + :282.0947,found:282.0944.

Embodiment 2

[0034] Add 41.2mg (0.3mmol) thioamide and 58.5mg (0.45mmol) alkyne aldehyde into a 10mL reaction flask with a stirring bar, add 3mL (0.033M) ethanol at room temperature, and then add 14.0mg (0.015mmol) catalyst CuBr (PPh 3 ) 3 and 30.6 mg (0.3 mmol) of pivalic acid, stirred at 60° C. for 8 hours, spin-dried and separated by silica gel chromatography to obtain the target product with a yield of 77%.

[0035]

[0036] Thiazole Heterocyclic Compounds 1 H NMR, 13 C NMR, HR-ESI-MS spectrogram data are as follows:

[0037] 1 H NMR (400MHz, CDCl3): δ7.89(d, J=9.8Hz, 2H), 7.59(s, 1H), 7.47-7.32(m, 8H), 5.63(s, 1H), 3.63-3.54(m ,2H),1.29(t,J=7.0Hz,3H).

[0038] 13 C NMR (101MHz, CDCl3): δ169.0, 141.7, 141.2, 133.8, 130.1, 129.0, 128.8, 128.3, 126.7, 126.5, 77.6, 64.8, 15.4.

[0039] HR-MALDI-MS: m / z calcd.for C 18 h 17 NOS[M+H] + :296.1104,found:296.1104.

Embodiment 3

[0041] Add 41.2mg (0.3mmol) of thioamide and 58.5mg (0.45mmol) of alkyne aldehyde substrate into a 10mL reaction flask with a stirring bar, add 3mL (0.033M) of isopropanol at room temperature, and then add 14.0mg (0.015 mmol) Catalyst CuBr(PPh 3 ) 3 and 30.6 mg (0.3 mmol) of pivalic acid, stirred at 60° C. for 8 hours, spin-dried and separated by silica gel chromatography to obtain the target product with a yield of 74%.

[0042]

[0043] Thiazole Heterocyclic Compounds 1 H NMR, 13 C NMR, HR-ESI-MS spectrogram data are as follows:

[0044] 1 H NMR (400MHz, CDCl3): δ7.89(d, J=3.9Hz, 2H), 7.55(s, 1H), 7.46-7.36(m, 8H), 5.74(s, 1H), 3.79-3.73(m ,1H),1.24(dd,J=14.6,6.1Hz,6H).

[0045] 13 C NMR (101MHz, CDCl3): δ169.0, 141.5, 141.0, 133.8, 130.1, 129.0, 128.7, 128.2, 126.8, 126.5, 74.8, 69.8, 22.5, 22.2.

[0046] HR-MALDI-MS: m / z calcd.for C 19 h 19 NOS[M+H] + :310.1260,found:310.1256.

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Abstract

The invention discloses a method for preparing functionalized thiazole heterocyclic compounds through a Cu (I) catalyzed multi-component cyclization reaction, and applications of the functionalized thiazole heterocyclic compounds, and belongs to the field of chemical synthesis. According to the method, Cu (I) is mainly used for catalysis, protonic acid such as pivalic acid is used as an additive,thioamide, aryl alkyne aldehyde and alcohol can be subjected to a series of domino cyclization reactions under the reaction condition of 55-65 DEG C to obtain the diversified functionalized thiazole heterocyclic compounds. The preparation method is simple to operate, simple and efficient in the used catalytic system, friendly to the environment, wide in substrate application range of thioamide, aryl alkyne aldehyde and alcohol and good in regioselectivity, various functionalized thiazole heterocyclic compounds can be efficiently synthesized, and the compounds have a wide application prospect in the aspects of bioactive molecules and drug development.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method and application for preparing a functionalized thiazole heterocyclic compound through Cu(I)-catalyzed multi-component cyclization reaction. Background technique [0002] Thiazoles are an important class of organic heterocyclic molecules with special structures, which are often used in bioactive molecules, drugs and functional organic materials. Active molecules containing thiazole structural units such as TAK-715, Ro 61-8048, NCH-31 and abafungin have powerful physiologically active functions, including anti-cancer, anti-virus, anti-fungal, anti-tumor, etc. In recent decades, the synthesis of thiazoles has received extensive attention. Transition metal-catalyzed coupling reactions of parent thiazole molecules are an important method for the synthesis of functionalized thiazoles. However, the thiazole parent compound must undergo halogenation or metal prefu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/24A01N43/78A01P7/00A01P7/04
CPCA01N43/78C07D277/24
Inventor 曹华余跃
Owner GUANGDONG PHARMA UNIV
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