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Synthesis method of 2-alkylthio polysubstituted furan derivative

The technology of a furan derivative and a synthesis method is applied in the field of synthesis of 2-alkylthio polysubstituted furan derivatives, can solve problems such as complicated reaction steps and the like, achieves low cost, mild reaction conditions, and cheap and easy-to-obtain raw materials Effect

Pending Publication Date: 2022-04-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above methods all require multi-step reactions to obtain 2-alkylthio polysubstituted furan derivatives. The reaction steps are cumbersome and require the use of odorous and toxic thiols.

Method used

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  • Synthesis method of 2-alkylthio polysubstituted furan derivative
  • Synthesis method of 2-alkylthio polysubstituted furan derivative
  • Synthesis method of 2-alkylthio polysubstituted furan derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] In a 25 mL schlenk tube, add 3,3-dimethylthio-2-propen-1-one 2a (0.5 mmol), acetophenone 3a (1.0 mmol), cuprous iodide (10 mol%) sequentially under argon , di-tert-butyl peroxide (1.0 mmol) and 5.0 mL of benzotrifluoride, stirred at 100° C. for 20 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=70:1) to obtain the target product 1a (110 mg, yield 75%). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0034] Typical Compound Characterization Data

[0035] 2-Alkylthio polysubstituted furan derivatives (1a), light yellow oily liquid. 1 H NMR (400MHz, CDCl 3 )δ7.76(d, J=7.3Hz, 2H), 7.54(d, J=7.5Hz, 2H), 7.47(d, J=7.3Hz, 1H), 7.41(t, J=7.4Hz, 2H) ,7.31(t,J=7.7Hz,2H),7.21(t,J=7.4Hz,1H),6.86(s,1H),2.61(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ189.3, 158.2, 154.1, 1...

Embodiment 2

[0037] The reaction steps and operations are the same as in Example 1, except that the molar ratio of 2a and 3a is 1:1.5. The reaction was stopped, and the target product 1a (103 mg, yield 70%) was obtained after post-treatment.

Embodiment 3

[0039] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is that catalyst is CuCl 2 . The reaction was stopped, and the target product 1a (88 mg, yield 60%) was obtained after post-treatment.

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Abstract

The invention discloses a synthesis method of a 2-alkylthio polysubstituted furan derivative. Ketene dithioacetal and aryl methyl ketone which are easy to prepare and have structural diversity and multiple reaction centers are used as raw materials, the 2-alkylthio polysubstituted furan derivative is generated in one step through intermolecular oxidation cross-coupling and intramolecular cyclization reaction, and the obtained polysubstituted furan derivative has certain potential drug activity and can be used for preparing drugs. And functional products can be further generated through conversion. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high reaction efficiency and diversity of functional groups.

Description

technical field [0001] The invention belongs to the technical field of chemical organic synthesis, and relates to a synthesis method of 2-alkylthio polysubstituted furan derivatives. Background technique [0002] As an important class of heterocyclic compounds, multi-substituted furan derivatives are the core skeleton of many natural products and physiologically active compounds. Synthetic important intermediates have received extensive attention from organic chemists. Among them, the 2-alkylthio group in the 2-alkylthio multi-substituted furan skeleton structure is a group that can be further functionalized, and can be used as an intermediate in the structure of drugs and chemical products. Therefore, it is simple and convenient to synthesize 2-alkylthio multi-substituted Furan derivatives are of great interest. At present, the methods for synthesizing 2-alkylthio polysubstituted furans mainly include: 1) Starting from dithioketene, alkylating with formaldehyde and mercap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/64C07D409/06C07D307/68C07D405/06C07D409/04C07D307/46
CPCC07D307/64C07D409/06C07D307/68C07D405/06C07D409/04C07D307/46
Inventor 余正坤吴苹周永贵
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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