Lactamide compounds and preparation method thereof

A technology for internal sulfonamides and compounds, applied in the field of internal sulfonamide compounds and their preparation, can solve the problems of difficult acquisition, complex catalyst structure, and high price, and achieve the effects of simple reaction operation, reduction of heavy metal residues, and high reaction efficiency

Active Publication Date: 2021-04-02
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In short, these methods have disadvantages such as complex catalyst structure, not easy to obtain, and expensive. More importantly, the reaction substrates of these methods are limited to arylsulfonyl azide substrates, which can only be used to synthesize rigid benzos. endosulfonamide product

Method used

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  • Lactamide compounds and preparation method thereof
  • Lactamide compounds and preparation method thereof
  • Lactamide compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: Taking phenylpropanesulfonamide as standard substrate, reaction conditions for the synthesis of iron-catalyzed endosulphonamide

[0047]

[0048]

[0049] research:

[0050] Among them, footnote a indicates that the reaction is operated at 60 degrees Celsius; footnote b indicates that molecular sieves are not added to the reaction; wherein [Fe] is an iron salt; the ligand structure is shown in L1-L7 as shown in the table; mol% refers to the relative molar amount, and equiv represents Equivalent, base represents common inorganic base, solvent refers to organic solvent, the volume is 2mL; where DMF is N,N'-dimethylformamide, MeCN is acetonitrile, DCE is 1,2-dichloroethane, 1, 4-dioxane is dioxane, and toluene is toluene. Among them, ligand refers to a multidentate nitrogen ligand, oxidant refers to an oxidizing agent, and yield refers to the total NMR yield of endosulphonamide and endosulphonimide, with s-trimethoxybenzene as the internal standard. ...

Embodiment 2

[0055] 3-(4-Methylphenyl)isothiazolidine-1,1-dioxo[3-(4-Tolyl)isothiazolidine 1,1-dioxide]:

[0056]

[0057] First weigh ferrous perchlorate (5.1mg, 0.02mmol) and ligand L2 (8.2mg, 0.04mmol) into a 4mL reaction bottle, add 1.0mL acetonitrile to dissolve, stir at room temperature for 30 minutes, and in situ complexation When finished, weigh Molecular sieves (50.0mg), iodobenzene pivalate (163.8mg, 0.4mmol) and p-toluenepropanesulfonamide substrate (42.3mg, 0.2mmol) were added to the reaction system, and then 1.0mL of acetonitrile was added to dissolve, and at 80 At ℃, react for 2 h, filter, wash the filter cake with an appropriate amount of saturated sodium bicarbonate, extract the aqueous phase with dichloromethane 3 times (3×10 mL), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, and remove the solvent Afterwards, separated by column chromatography (dichloromethane / petroleum ether=1:1~dichloromethane) to obtain the sulfonamide 3...

Embodiment 3

[0059] 3-(4-Methoxyphenyl)isothiazolidine-1,1-dioxo[3-(4-Methoxyphenyl)isothiazolidine1,1-dioxide]

[0060]

[0061] White solid; yield 86%; 1 H NMR (400MHz, CDCl 3 )δ7.32(d,J=8.8Hz 2H), 6.90(d,J=8.8Hz 2H),4.79–4.63(m,1H),4.50(br s,1H),3.81(s,3H),3.45 –3.32 (m,1H),3.25–3.17(m,1H),2.76–2.68(m,1H),2.44–2.34(m,1H); 13 C NMR (100 MHz, CDCl 3 )δ159.8, 132.0, 127.5, 114.5, 58.0, 55.5, 48.5, 32.4; HRMS(ESI+) calc’d for C 10 h 13 NNaO 3 S[M+Na] + :250.0508, found 250.0513.

[0062] 3-Phenylisothiazolidine 1,1-dioxide

[0063]

[0064] white solid

[0065] 1 H NMR (400MHz, CDCl 3 ( m,1H),2.45–2.34(m,1H).

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PUM

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Abstract

The invention provides a sultam compound and a preparation method thereof. The method provided by the invention specifically comprises the following steps: putting a catalyst C, sulfamide B and an oxidant D into an organic solvent, performing a reaction, and performing separation purification so as to obtain a sultam compound E, or after a detection reaction is completed, adding an oxidant F, implementing a reaction, and performing separation purification so as to obtain a sulfonylimine compound G. The catalyst used in the method is an iron complex which is cheap and easy to obtain and low intoxicity. When sulfamide H is used, the reaction is completed according to the method, and under a condition that another oxidant F is additionally used, the sulfonylimine compound is synthesized by using a one-pot method. The prepared sultam compound and the sulfonylimine compound are widely applied to fields of medicine chemistry, material chemistry and organic synthesis.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an internal sulfonamide compound and a preparation method thereof. Background technique [0002] The sulfonamide structure skeleton widely exists in some drug macromolecules with broad-spectrum antibacterial activity. It is a very important class of structural fragments and plays an important role in the synthesis of new drugs. In particular, the internal sulfonamide structure has good water solubility and stability, is regarded as the equivalent of the lactam skeleton, and is widely used in the structural modification of drugs (such as image 3 Shown), so it has been widely concerned by scientists in the field of medicinal chemistry [a) Mustafa, A. Chem. Rev. 1954, 54, 195–223. b) Inagaki, M.; Tsuri, T.; Jyoyama, H.; Ono, T.; Yamada, K.; Kobayashi, M.; Hori, Y.; Arimura, A.; Yasui, K.; Ohno, K.; Kakudo, S.; Kato, M.; Kawai, S.; Matsumoto, S.J. Med. Chem. 2000, 43, 204...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/02C07D279/02C07D275/06C07F7/08C07D285/00C07D513/04C07D275/03
CPCC07D275/02C07D275/03C07D275/06C07D279/02C07D285/00C07D513/04C07F7/0812
Inventor 刘文博钟大猷刘卫吴笛
Owner WUHAN UNIV
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