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Synthetic method of alkynyl sulfone derivative

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harsh reaction conditions and the use of strong oxidants, and achieve good substrate applicability, environmental friendliness, and reaction The effect of safe and easy operation

Inactive Publication Date: 2017-04-19
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to overcome the shortcomings of existing alkynyl sulfone synthesis methods, such as harsh reaction conditions and the need to use strong oxidants, to provide a new alkynyl sulfone synthesis method

Method used

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  • Synthetic method of alkynyl sulfone derivative
  • Synthetic method of alkynyl sulfone derivative
  • Synthetic method of alkynyl sulfone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 1 H NMR (400MHz, CDCl 3 )δ7.96(d,J=8.3Hz,2H),7.51(d,J=7.1Hz,2H),7.46–7.44(m,1H),7.40-7.34(m,4H),2.46(s,3H ). 13 C NMR (100MHz, CDCl 3 ) δ 145.3, 138.9, 132.7, 131.4, 130.0, 128.6, 127.4, 118.0, 92.9, 85.6, 21.7.

Embodiment 2

[0034] Example 2: 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=7.9Hz, 2H), 7.39(t, J=8.7Hz, 4H), 7.16(d, J=7.7Hz, 2H), 2.46(s, 3H), 2.37(s, 3H). 13 C NMR (100MHz, CDCl 3 ) δ 145.2, 142.3, 139.1, 132.7, 129.9, 129.4, 127.4, 114.9, 93.7, 85.2, 21.8, 21.7.

Embodiment 3

[0035] Example 3: 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=8.0Hz, 2H), 7.43(d, J=7.9Hz, 2H), 7.38(d, J=8.0Hz, 2H), 7.19(d, J=7.9Hz, 2H) ,2.66(q,J=7.6Hz,2H),2.46(s,3H),1.20(t,J=7.6Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ 148.5, 145.4, 139.2, 132.8, 130.0, 128.3, 127.4, 115.1, 93.7, 85.3, 29.0, 21.7, 15.0.

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Abstract

The invention provides a synthetic method of an alkynyl sulfone derivative. The method is characterized in that alkynyl sulfone derivative is obtained through a reaction of alkynyl bromide and organic sodium sulfinate in the presence of an organic solvent and a strong acid used as a catalyst; and the organic solvent is one or more of toluene, chloroform, 1,2-dichloroethane, 1,4-dioxane and tetrahydrofuran. The method has the advantages of no use of complex reaction substrates or strong oxidants, simple and easily available reaction raw materials, safety and simplicity in reaction operation, environmentally-friendly reaction process, good substrate applicability, good function group tolerance, and high separation yield under preferable conditions and the alkynyl sulfone derivative synthesized through the method widely exists in natural products and medicine molecules, and also can be used as a very effective alkynylation reagent.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and particularly designs a new synthesis method of alkynyl sulfone derivatives. Background technique [0002] Sulfone compounds have a wide range of biomedical activities and are important structural units of many bioactive molecules and natural products. Alkynyl sulfone is an important part of sulfone compounds. Its structural unit not only has biological activity, but also a very important class of organic synthons, and is widely used as an alkynyl source in alkynylation reactions. Because of the importance of alkynyl sulfone compounds, people have been studying their synthetic methods. (C. Kuhakarn, et al. J. Org. Chem. 2016, 81, 2744–2752; X. Huang, et al. Tetrahedron Lett. 2002, 43, 1059–1061; N. Singh, et al. Org. Lett. 2015, 17, 2656-2659; W.J.Moran, etal.Org.Biomol.Chem.2014, 12, 4156-4162) The synthesis methods that have been reported now mainly include: 1. Coupling reaction ...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/14
CPCC07C315/00C07C317/14
Inventor 唐晓冬戴晨舒朱秋华
Owner SOUTHERN MEDICAL UNIVERSITY