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Polysubstituted isothiazole derivative and preparation method thereof

A technology for isothiazole and derivatives, applied in the field of polysubstituted isothiazole derivatives and their preparation, can solve the problems of difficult preparation of raw materials, poor atom economy, etc., and achieve the effects of avoiding heavy metal pollution, easy operation and high reaction efficiency

Active Publication Date: 2021-12-31
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of this method are moderate yields, difficult preparation of starting materials, and poor atom economy

Method used

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  • Polysubstituted isothiazole derivative and preparation method thereof
  • Polysubstituted isothiazole derivative and preparation method thereof
  • Polysubstituted isothiazole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1: The raw material tert-butylsulfinamide derivative compound 1 (381mg, 1mmol) was added in a round bottom flask, and methylene chloride (10mL) was added in the round bottom flask, and after dissolving, DMAP was added at 0°C ( 305mg, 2.5mmol), TFAA (556μL, 4mmol), reacted at 0°C for 10min, then raised the temperature to 25°C for 12h, after the reaction was completed, the solvent was distilled off under reduced pressure, and the product was separated by silica gel column chromatography, and the eluent was petroleum Ether / ethyl acetate (volume ratio 20:1) to obtain polysubstituted isothiazole product 1 (308mg).

[0075]6-(3-(4-methoxyphenyl)-5-(trifluoromethyl)isothiazol-4-yl)-2,2-dimethyl-4H-1,3-dioxin-4-one, yield 80%;

[0076]

[0077] 1 H NMR (400MHz, Chloroform-d) δ7.56 (d, J = 9.0Hz, 2H), 6.95 (d, J = 8.4Hz, 2H), 5.42 (s, 1H), 3.84 (s, 3H), 1.70 (s,6H). 13 C NMR (101MHz, Chloroform-d) δ168.20, 161.27, 160.01, 158.67, 155.97 (q, 2 J C-F =3.6Hz), 129.9...

Embodiment 2

[0078] Example 2: The raw material tert-butylsulfinamide derivative compound 1 (385mg, 1mmol) was added in a round-bottomed flask, and chloroform (10mL) was added to the round-bottomed flask, and after dissolving, DMAP was added at 0°C ( 305mg, 2.5mmol), TFAA (556μL, 4mmol), reacted at 0°C for 12min, then raised the temperature to 50°C for 12h, after the reaction, the solvent was distilled off under reduced pressure, and the product was separated by silica gel column chromatography, and the eluent was petroleum Ether / ethyl acetate (volume ratio 20:1) to obtain multi-substituted isothiazole product 2 (175 mg);

[0079] 6-(3-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)-2,2-dimethyl-4H-1,3-dioxin-4-one, yield 45%;

[0080]

[0081] 1 H NMR (400MHz, Chloroform-d) δ7.57(d, J=8.6Hz, 2H), 7.44(d, J=8.5Hz, 2H), 5.44(s, 1H), 1.70(s, 6H). 13 C NMR (101MHz, Chloroform-d) δ167.03, 159.66, 158.02, 158.67, 156.37 (q, 2 J C-F =3.6Hz), 136.67, 131.84, 129.65, 129.11, 120.69 (q,...

Embodiment 3

[0082] Example 3: The raw material tert-butylsulfinamide derivative compound 1 (369mg, 1mmol) was added to a round bottom flask, and chloroform (10mL) was added to the round bottom flask, and after dissolving, DMAP was added at 0°C ( 305mg, 2.5mmol), TFAA (556μL, 4mmol), reacted at 0°C for 10min, then raised the temperature to 50°C for 12h, after the reaction was completed, the solvent was distilled off under reduced pressure, and the product was separated by silica gel column chromatography, and the eluent was petroleum Ether / ethyl acetate (volume ratio 30:1), to obtain multi-substituted isothiazole product 3 (183mg);

[0083] 6-(3-(4-fluorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)-2,2-dimethyl-4H-1,3-dioxin-4-one, yield 63%;

[0084]

[0085] 1 H NMR (400MHz, Chloroform-d) δ7.63–7.59 (m, 2H), 7.14 (d, J=1.9Hz, 2H), 5.43 (s, 1H), 1.68 (s, 6H). 13 C NMR (101MHz, Chloroform-d) δ167.31, 163.98 (d, 1 J C-F =250.0Hz), 159.77, 158.21, 156.32 (q, 2 J C-F =38.0Hz), 130.50(...

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Abstract

The preparation method comprises the following steps: adding one of trifluoroacetic anhydride, difluoroacetic anhydride and oxalyl chloride monoester and dimethylaminopyridine into a solvent, or jointly adding one of trifluoroacetic anhydride, difluoroacetic anhydride and oxalyl chloride monoester, dimethylaminopyridine and sodium hydrocarbon acid into the solvent, and stirring the solution to obtain the polysubstituted isothiazole derivative; then performing stirring reaction with a compound 1 at 0 DEG C for 10-20 minutes, heating the mixture to 25-50 DEG C, and performing stirring reaction to generate a compound 2. The method provided by the invention has the advantages of short steps, mild conditions, low cost and wide universality, does not need to use high-toxicity reagents and rare and noble metal reagents, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a multi-substituted isothiazole derivative and a preparation method thereof. Background technique [0002] Sulfur-containing heterocycles are very important skeleton structures in organic heterocycles, and they exist in many drug molecules and natural products with biological activity. Isothiazole is an important class of five-membered aromatic nitrogen-sulfur heterocyclic compounds, which is an important structure in modern drug discovery. Ziprasidone) also has biological activities such as anticancer, antidiabetic, antifungal and neuroprotective. Multi-substituted isothiazole derivatives are also widely used in pesticides, chemical reagents, photoelectric materials, industry, dyes, polymer additives and other fields. Its two electronegative heteroatoms are in a 1,2-relationship, although there are related 1,2-oxazoles such as isoxazoles and pyrazole. Due to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14C07D275/03
CPCC07D417/04C07D417/14C07D275/03
Inventor 张洪彬李瑞魏凯陈文李良羊晓东罗晓东
Owner YUNNAN UNIV
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