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Novel method for preparing thiophene formaldehyde compounds

A technology of thiophene formaldehyde and compounds, which is applied in the field of preparation of multi-substituted thiophene formaldehyde compounds, can solve the problems of complex reaction steps, high industrial cost, harsh reaction conditions, etc., and achieve the effects of short reaction time, simple operation and simple preparation

Active Publication Date: 2019-07-16
LANZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] The technical problem to be solved by the present invention is to provide a novel method for preparing a multi-substituted thiophene formaldehyde compound in view of the above-mentioned problems of harsh synthetic reaction conditions, complex reaction steps, and high industrial cost in the prior art

Method used

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  • Novel method for preparing thiophene formaldehyde compounds
  • Novel method for preparing thiophene formaldehyde compounds
  • Novel method for preparing thiophene formaldehyde compounds

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1: the preparation method of the present embodiment comprises the following steps:

[0038] Add compound Ia (0.06mol, 10.0g), potassium sulfide (0.18 mol, 20.4g), dimethyl sulfoxide (300mL) sequentially into a 500mL round bottom flask, and stir the reaction at 140°C for 8h, thin-layer chromatography Monitor the reaction process until the reaction is complete; add water to quench the reaction, extract three times with 1.5L ethyl acetate, combine the organic phases, evaporate the ethyl acetate under reduced pressure, and recrystallize and purify with petroleum ether / ethyl acetate to obtain polysubstituted thiophene carboxaldehyde Compound IIa, yield 72%. The reaction equation is as follows:

[0039]

[0040] references

[0041] 1. (a). J. Cossy, N. Blanchard and C. Meyer, Tetrahedron Letters, 2002, 43, 1801-1805; (b). K. Sakaguchi, M. Fujita and Y. Ohfune, Tetrahedron Letters, 1998, 39, 4313-4316; (c). Y. Maeda, T. Nishimura and S. Uemura, Chemistry Lette...

Embodiment 2

[0056] The structure, NMR, and high-resolution mass spectrometry data of the product obtained in Example 2 are as follows:

[0057]

[0058] 1H NMR (400MHz, CDCl 3 ,ppm):δ=9.96(s,1H),7.80(d,J=1.2Hz,1H), 7.63(s,1H),7.30-7.25(m,2H),2.34(s,3H); 13 C NMR (100MHz, CDCl 3 , ppm): δ=183.0, 144.2, 143.6, 137.9, 134.7, 131.5, 129.7, 129.0, 126.1, 21.1; HRMS calcd for C 12 h 11 OS[M+H] + 203.0525; found: 203.0529.

Embodiment 3

[0059] The structure of embodiment 3 gained product, NMR, high-resolution mass spectrum data are as follows:

[0060]

[0061] 1 H NMR (400MHz, CDCl 3 ,ppm):δ=9.95(d,J=1.2Hz,1H),7.79(d,J=1.2Hz,1H),7.61(s,1H),7.18-7.16(d,J=8.0Hz,1H) ,7.11-7.09(d,J=8.0Hz,2H),2.35(s,3H),2.30(s,3H); 13 C NMR (100MHz, CDCl 3 , ppm): δ=183.0, 143.7, 143.4, 137.5, 135.6, 134.6, 132.3, 132.2, 130.6, 130.2, 128.8, 20.8, 20.1; HRMS calcd for C 13 h 13 OS[M+H] + 217.0682; found: 217.0687.

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Abstract

The present invention provides a novel method for preparing thiophene formaldehyde compounds by using cyclopropylethanol and K2S under metal-free catalytic conditions. The thiophene formaldehyde compounds are directly synthesized by using cyclopropylethanol as a substrate and dimethyl sulfoxide as a solvent. One of the significant advantages of the reaction is that dimethyl sulfoxide is both a solvent and an oxidant in the reaction, so that the need for additional oxidants for the reaction is avoided. Secondly, using inorganic sulfur reagent, potassium sulfide, as a source of sulfur is low-cost, environmentally friendly and in line with the current requirements of atomic economy and green chemistry, and also avoids the pre-functionalization of the starting materials. At the same time, theraw materials used in the invention are simple to prepare, cheap and easy to obtain. The invention also has advantages of being safe in operation and high in yield, and has great industrial application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a novel multi-substituted thiophene formaldehyde compound. Background technique [0002] Cyclopropane is an important intermediate in the synthesis of heterocyclic compounds. For example, groups such as Meyer, Ohfune, and Uemura have reported the conversion of cyclopropanols to homoenols or halides. 1 However, through the literature, we found that there are few reports on the construction of heterocyclic rings by using cyclopropyl alcohols through C-C bond cleavage and cyclization. 2 [0003] Thiophene aldehydes and their derivatives are an important class of heterocyclic compounds. These compounds are not only the core structural units of many natural products, but also mostly have biological activity. They are widely used in biochemistry, natural product synthesis, drug synthesis and materials chemistry. and so on have a wide ran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22
CPCC07D333/22
Inventor 严汝龙王婷
Owner LANZHOU UNIVERSITY
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