Synthetic method of diaryl sultam compounds

A technology of sultam and synthesis method, which is applied in the field of synthesis of diaromatic sultam compounds, can solve the problems of small applicable range of raw materials, harsh reaction conditions, etc., and achieves wide substrate applicability, simple reaction operation, and reaction Simple effect of raw materials

Active Publication Date: 2018-10-02
SHAANXI NORMAL UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

The synthesis methods of these dibenzosultams are all intramolecular cyclization reactions, and there are some disadvantages in varying degrees: the need for pre-functionalization, especially halogenated substrates, small application range of raw materials, harsh reaction conditions, etc.
In addition, there is no literature on the synthesis of diarylsultam compounds through the cyclization reaction of C–H bond functionalization.

Method used

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  • Synthetic method of diaryl sultam compounds
  • Synthetic method of diaryl sultam compounds
  • Synthetic method of diaryl sultam compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Taking the preparation of 6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0018]

[0019] Add 37.41mg (0.2mmol) N-methoxybenzenesulfonamide, 4.48mg (0.02mmol) palladium acetate, 72.7mg (0.4mmol) anhydrous copper acetate, 28.43mg (0.2mmol) in a 10mL pressure reaction tube in sequence Sodium pivalate hydrate, 100mg dry Molecular sieve, 121.52mg (0.8mmol) of cesium fluoride, 2.7mL of dioxane, 0.3mL of dimethyl sulfoxide, 119.3mg (0.4mmol) of benzene acetylene, under argon protection, a closed system at 110°C, stirring for 24h, reaction After the end, cool to room temperature, extract, combine the organic phases, anhydrous Na 2 SO 4 Dry and remove the organic solvent under reduced pressure. Dichloromethane is used as the eluent. The crude product is separated by silica gel column chromatography to obtain 6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide The separation yiel...

Embodiment 2

[0022] Taking the preparation of 2-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0023]

[0024] In Example 1, the N-methoxybenzenesulfonamide used was replaced with equimolar N-methoxy-4-methylbenzenesulfonamide, and the other steps were the same as in Example 1, to obtain 2-methyl-6H -Dibenzo[c,e][1,2]thiazine-5,5-dioxide, the separation yield is 83%, and the structural characterization data are as follows:

[0025] 1 H NMR(400MHz, DMSO-d 6 )δ (ppm) = 11.31 (s, 1H), 8.22 (d, J = 8.0 Hz, 1H), 8.09 (s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.48 (t, J = 8.2Hz, 2H), 7.31 (t, J = 7.7 Hz, 1H), 7.22 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H); 13 C NMR(100MHz, DMSO-d 6 )δ(ppm)=142.8,136.7,132.0,131.7,130.2,129.1,125.7,125.3,123.7,121.4,121.1,119.5,21.3; HRMS(ESI)m / z: C 13 H 11 NO 2 S[M+Na] + The theoretical value is 268.0403, and the measured value is 268.0393.

Embodiment 3

[0027] Taking the preparation of 2-tert-butyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0028]

[0029] In Example 1, the N-methoxybenzenesulfonamide used was replaced with equimolar N-methoxy-4-tert-butylbenzenesulfonamide, and the other steps were the same as in Example 1, to obtain 2-tert-butyl -6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide, the separation yield is 86%, and the structural characterization data are as follows:

[0030] 1 H NMR(400MHz, DMSO-d 6 )δ(ppm)=11.29(s,1H), 8.30(d,J=8.0Hz,1H), 8.14(s,1H), 7.86(d,J=8.2Hz,1H), 7.70(d,J= 8.3Hz, 1H), 7.46 (t, J = 7.7 Hz, 1H), 7.30 (t, J = 7.7 Hz, 1H), 7.20 (d, J = 8.0 Hz, 1H), 1.38 (s, 9H); 13 C NMR(100MHz,DMSO-d6)δ(ppm)=155.5,136.7,132.0,131.5,130.2,125.6,125.5,123.8,122.1,121.7,121.1,119.5,35.2,30.8; HRMS(ESI)m / z: C 16 H 17 NO 2 S[M+Na] + The theoretical value is 310.0872, and the measured value is 310.0858.

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Abstract

The invention discloses a synthetic method of diaryl sultam compounds. According to the method, transition metal palladium is taken as a catalyst, N-methoxybenzenesulfonamide compounds and aryne precursors are subjected to a cyclization reaction based on functionalization of a C-H bond in an ortho-position of -SO2NHOMe in N-methoxybenzenesulfonamide in presence of fluoride, and a series of diarylsultam compounds are synthesized efficiently and conveniently. The method has the advantages of simple and easily available raw materials, simple reaction operation, high substrate applicability, highatom utilization ratio and the like.

Description

Technical field [0001] The present invention relates to a method for synthesizing diaromatic sultam compounds. Specifically, it uses transition metal palladium as a catalyst and passes through N-methoxybenzenesulfonamide compounds and alkyne in the presence of fluorides. Based on N-methoxybenzenesulfonamide in -SO 2 NHOMe ortho-position C-H bond functionalized cyclization reaction to synthesize diaromatic sultam compounds. Background technique [0002] Sultan is an important functional group, among which the diaromatic sultam skeleton is an important organic component of many drug molecules and natural products with biological activity. For example, the diaromatic sultam backbone is present in many anti-inflammatory drug molecules (Bioorg.Med.Chem.Lett.1999, 9:673–678; Tetrahedron Lett.2008, 49:2320–2323; Bioorg.Med. Chem. Lett. 2008, 18: 329-335). [0003] The methods for synthesizing diaromatic sultams reported in the literature mainly include (I) intramolecular free radical cy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/02C07D513/04
CPCC07D279/02C07D513/04
Inventor 李靖冯思敏李珊魏俊发
Owner SHAANXI NORMAL UNIV
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