A kind of method and application of functionalized thiazole heterocyclic compound prepared by cu(i) catalyzed multi-component cyclization reaction

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

Active Publication Date: 2021-10-12
GUANGDONG PHARMA UNIV
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  • Abstract
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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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  • A kind of method and application of functionalized thiazole heterocyclic compound prepared by cu(i) catalyzed multi-component cyclization reaction
  • A kind of method and application of functionalized thiazole heterocyclic compound prepared by cu(i) catalyzed multi-component cyclization reaction
  • A kind of method and application of functionalized thiazole heterocyclic compound prepared by cu(i) catalyzed multi-component cyclization reaction

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 41.2 mg (0.3 mmol) thiocyanamide, 58.5 mg (0.45 mmol) of aldehyde was added to 10 ml of a reaction bottle with a stirrer, and 3 ml (0.033 m) methanol was added at room temperature, and then 14.0 mg (0.015 mmol) catalyst CUbr (PPH 3 ) 3 And 30.6 mg (0.3 mmol) of specialty acid, stirred at 60 ° C for 8 hours, and the target product was separated by silica gel chromatography at 60 ° C, and the yield was 79%.

[0028]

[0029] Thiazole heterocyclic compound 1 H NMR, 13 C NMR, HR-ESI-MS spectrum data is as follows:

[0030] 1 H NMR (400MHz, CDCL 3 : Δ7.89 (D, J = 3.5 Hz, 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 Hide 15 NOS [M + H] + : 282.0947, Found: 282.0944.

Embodiment 2

[0034] 41.2 mg (0.3 mmol) thiocyanlamide, 58.5 mg (0.45 mmol) aconene was added to a reaction bottle with a stirrer, and 3 ml (0.033 m) ethanol was added at room temperature, and then 14.0 mg (0.015 mmol) catalyst CUbr (PPH 3 ) 3 And 30.6 mg (0.3 mmol) of specialty acid, stirred at 60 ° C for 8 hours, and the target product was separated by silica gel chromatography after drying. The yield was 77%.

[0035]

[0036] Thiazole heterocyclic compound 1 H NMR, 13 C NMR, HR-ESI-MS spectrum data is as follows:

[0037] 1 H NMR (400MHz, CDCL3): Δ7.89 (D, J = 9.8 Hz, 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 = 7.0 Hz, 3H).

[0038] 13 C NMR (101 MHz, 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 Hide 17 NOS [M + H] + : 296.1104, Found: 296.1104.

Embodiment 3

[0041] 41.2 mg (0.3 mmol) thiosamide, 58.5 mg (0.45 mmol) aldehyde substrate was added to a reaction bottle with stirred sub-reaction, and 3 ml (0.033m) isopropyl alcohol was added at room temperature, and then 14.0 mg (0.015) Mmol) Catalyst CUbr (PPH 3 ) 3 And 30.6 mg (0.3 mmol) of specialty acid, stirred at 60 ° C for 8 hours, and the target product was separated by silica gel chromatography after drying, and the yield was 74%.

[0042]

[0043] Thiazole heterocyclic compound 1 H NMR, 13 C NMR, HR-ESI-MS spectrum data is as follows:

[0044] 1 H NMR (400 MHz, CDCL3): Δ7.89 (D, J = 3.9 Hz, 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, 6.1 Hz, 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 Hide 19 NOS [M + H] + : 310.1260, Found: 310.1256.

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Abstract

The invention discloses a method and application for preparing a functionalized thiazole heterocyclic compound through a multi-component cyclization reaction catalyzed by Cu(I), and belongs to the field of chemical synthesis. This method is mainly catalyzed by Cu(I) and protonic acids such as pivalic acid as additives, thioamides, aryl alkynes and alcohols can undergo a series of domino cyclization reactions under the reaction conditions of 55‑65 °C , to obtain diverse functionalized thiazole heterocycles. The preparation method of the present invention is simple to operate, the catalytic system used is simple and efficient, and is environmentally friendly, and the substrates of thioamides, aryl alkynes and alcohols have a wide range of applications, good regioselectivity, and can efficiently synthesize a variety of functionalized Thiazole heterocyclic compounds have broad application prospects in the development of bioactive molecules and drugs.

Description

Technical field [0001] The present invention belongs to the field of chemical synthesis, and more particularly to a method and application of a functional chemical thiazole heterocyclic compound by catalytic multi-component reaction to Cu (I). Background technique [0002] The thiazole compound is an important and special organic heterocyclic molecule, which is often used in biologically active molecules, drugs and functional organic materials. The active molecules containingothothiazole structural units such as Tak-715, RO 61-8048, NCH-31, and ABAFungin have powerful physiological activity, including anti-cancer, antiviral, antifungal, anti-tumor, and the like. In recent decades, synthetic thiazole compounds have been widely concerned. The coupling reaction of the parent thiazole molecule catalyzed by the transition metal is an important method of synthesizing functional chemical thiazole compounds. However, thiazole mother compounds must pass through the halogenation or metal p...

Claims

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Application Information

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Patent Type & Authority Patents(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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