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A kind of synthetic method of N-arylthio sulfoximine
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A technology for arylthio sulfoximine and heteroarylthio sulfoximine is applied in the field of catalytic synthesis of N-arylthio sulfoximine derivatives, and can solve the problems of many reaction steps, harsh reaction conditions, limitations, etc. problem, to achieve the effect of easy handling, mild reaction conditions and strong operability
Active Publication Date: 2018-05-01
CHANGZHOU UNIV
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For example: the solvent and reaction substrate are relatively limited, the reaction steps are many, the reaction has gone through a nucleophilic process, and the reaction conditions are harsh, etc.
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Embodiment 1
[0020] Mix diphenyl sulfoximine 1a (2mmol), diphenyl disulfide 2a (2mmol) and cuprous bromide (0.2mmol), add 5 mL of chlorobenzene as a solvent, and react under heating. The reaction time is 5 hours. The conversion of diphenylsulfoximine was 100%, and the yield of 3aa was 94%. 1 H NMR (CDCl 3 ,400MHz):δ8.10-8.00(m,4H),7.60-7.45(m,8H),7.28(t,J=8.0Hz,2H),7.10(t,J=8.0Hz,1H); 13 C NMR (CDCl 3 ,100MHz): δ142.1, 139.9, 133.2, 129.3, 128.5, 128.4, 125.0, 123.9.
Embodiment 2
[0022] Mix bis(4-methylphenyl)sulfoximine 1b (2mmol), diphenyl disulfide 2a (2mmol) and copper chloride (0.2mmol), add N,N-dimethylformamide 5mL as solvent , Reacted under heating, and the reaction time was 12 hours. The conversion of bis(4-methylphenyl)sulfoximine was 100%, and the yield of 3ba was 89%. 1 H NMR (CDCl 3 ,400MHz):δ7.94-7.87(m,4H),7.46-7.44(d,2H),7.32-7.25(m,6H),7.10-7.07(m,1H),2.41(s,6H); 13 CNMR (CDCl 3 ,100MHz): δ144.0, 142.4, 137.2, 129.9, 128.4, 128.3, 124.8, 123.7, 21.5.
Embodiment 3
[0024] Mix bis(4-chlorophenyl)sulfoximine 1c (2mmol), diphenyl disulfide 2a (2mmol) and cuprous oxide (0.2mmol), add dimethyl sulfoxide 5mL as solvent, and heat In case of reaction, the reaction time is 15 hours. The conversion of bis(4-chlorophenyl)sulfoximine was 100%, and the yield of 3ca was 90%. 1 H NMR (CDCl 3 ,400MHz): δ7.95-7.92(m,4H),7.51-7.42(m,6H),7.31-7.27(m,2H),7.13(t,J=8.0Hz,1H); 13 C NMR (CDCl 3 ,100MHz): δ141.4, 140.2, 138.1, 129.9, 129.7, 128.5, 125.4, 124.2.
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Abstract
The invention relates to the field of medicines, pesticides, organic chemical industry and fine chemical industry, in particular to a simple, clean and efficient N-arylthiosulfoximine synthesis method. The method adopts sulfoximine and diaryl disulphide as raw materials and metallic copper salt as a catalyst. In application of the method, reaction time is 5-20h under conditions of heating and stirring, a mole ratio of the sulfoximine to the diaryl disulphide is 1:0.7-2, the Cu catalyst amount is 10% of the mole number of the sulfoximine, and high-yield N-arylthiosulfoximine derivatives can be obtained by reaction for 5-20h under stirring and heating at 25-100 DEG C. The method has advantages that due to adoption of the diaryl disulphide which is safe and easy to acquire as an arylthio source, adoption of high-toxicity benzene sulfenyl chloride adopted in previous methods is avoided, reaction operability is greatly improved, and a substrate range is expanded; in addition, the method is simple in operation and convenient for aftertreatment and is a simple and practical method for synthesis of the compounds.
Description
technical field [0001] The invention relates to the fields of medicine, pesticide, organic chemical industry and fine chemical industry, in particular to a method for catalytically synthesizing N-arylthio sulfoximine derivatives. Background technique [0002] Sulfoximine is an important class of organic synthesis intermediates and drug molecular skeleton structures, and its derivatives are widely used in the fields of pesticides and medicine. In addition, this type of structure can also be used as an excellent ligand for metal-catalyzed asymmetric organic synthesis reactions, and it is also an important organic synthesis intermediate in the field of fine chemicals. Therefore, the derivatization reaction of sulfoximine structure has important theoretical and practical significance. [0003] N-S bonds widely exist in natural product molecules in nature, and there have been many studies on the formation reactions of N-S bonds. However, for the structure of important organic c...
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