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Beta-carbonyl-(alpha-cyanoimine) compound and synthesis method thereof

A technology of cyanoimines and compounds, which is applied in the field of β-carbonyl-like compounds and their synthesis, can solve problems such as difficult sources of raw materials and substrates, expensive raw materials preparation, harsh reaction conditions, etc., and achieve good substrate adaptability and raw materials The effect of easy availability and simple ingredients

Inactive Publication Date: 2019-08-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In summary, there are mainly the above methods for the synthesis of β-carbonyl-(α-cyanoimine) compounds, but the types of compound products that can be synthesized by the above methods are relatively limited, and the sources of raw materials and substrates are difficult and complicated. , it is often obtained through several steps of reaction, and the preparation of raw materials is relatively expensive; or the reaction conditions are relatively harsh, it is not easy to popularize, and the reaction cost is relatively high

Method used

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  • Beta-carbonyl-(alpha-cyanoimine) compound and synthesis method thereof
  • Beta-carbonyl-(alpha-cyanoimine) compound and synthesis method thereof
  • Beta-carbonyl-(alpha-cyanoimine) compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: (E)-N-(tert-butyl)-2-oxo-2-phenylacetimidocyanide

[0027] (E)-N-(tert-butyl)-2-oxo-2-phenylacetimido cyanide adopts the following steps: 1. add 4.93 grams of benzyl tert-butyl ether in 1000 milliliters of reaction kettle, 13.60 Milliliter tert-butylisonitrile, 0.78 g silver trifluoromethanesulfonate, 13.60 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 300 ml chlorobenzene, heated to 80°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, cool to room temperature. The product was extracted with ethyl acetate, washed with saturated brine, and dried with a rotary evaporator to remove the solvent to obtain a crude product; ③The crude product was purified by column chromatography (petroleum ether:ethyl acetate=100:1) to obtain 5.3 g ( E)-N-(tert-butyl)-2-oxo-2-phenylacetimidocyanide, its structural formula is: The yield was 82%. Melting point: 34-35°C.

[0028] IR(KBr,cm -1 ):3737,2975,2929,...

Embodiment 2

[0033] Example 2: (E)-N-(tert-butyl)-2-oxo-2-(p-tolyl)iminoacetyl cyanide

[0034] (E)-N-(tert-butyl)-2-oxo-2-(p-tolyl)iminoacetyl cyanide adopts the following steps: 1. add 5.35 grams of p-methylbenzyl in 1000 milliliters of reaction kettle tert-butyl ether, 13.60 ml tert-butylisonitrile, 0.78 g silver triflate, 13.60 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 300 ml chlorobenzene , heated to 80°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, cool to room temperature. The product was extracted with ethyl acetate, washed with saturated brine respectively, and after drying, the solvent was removed with a rotary evaporator to obtain a crude product; ③The crude product was purified by column chromatography (petroleum ether:ethyl acetate=100:1) to obtain 5.76 g ( E)-N-(tert-butyl)-2-oxo-2-(p-tolyl)iminoacetyl cyanide, its structural formula is: The yield was 84%. Melting point: 60-61°C.

[0035] IR(KB...

Embodiment 3

[0040] Example 3: (E)-N-(tert-butyl)-2-(4-methoxyphenyl)-2-oxoiminoacetyl cyanide

[0041] (E)-N-(tert-butyl)-2-(4-methoxyphenyl)-2-oxoiminoacetyl cyanide adopts the following steps: 1. add 5.83 grams in 1000 milliliters reactor p-methoxybenzyl tert-butyl ether, 13.60 ml tert-butylisonitrile, 0.78 g silver triflate, 13.60 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 300ml of chlorobenzene was heated to 80°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, cool to room temperature. The product was extracted with ethyl acetate, washed with saturated brine respectively, and after drying, the solvent was removed with a rotary evaporator to obtain a crude product; ③The crude product was purified by column chromatography (petroleum ether:ethyl acetate=100:1) to obtain 5.86 g ( E)-N-(tert-butyl)-2-(4-methoxyphenyl)-2-oxoiminoacetyl cyanide, its structural formula is: The yield was 80%. Melting point: 38-39°C. ...

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Abstract

The invention relates to a beta-carbonyl-(alpha-cyanoimine) compound and a synthesis method thereof, wherein the compound has a structural formula defined in the specification, R<1> is hydrogen, methyl, methoxy, ester, fluorine, chlorine, bromine, alkenyl or alkynyl (C2-C3), R<2> is hydrogen or methyl, and R<3> is hydrogen or methyl. According to the present invention, the beta-carbonyl-(alpha-cyanoimine) compound is a valuable organic synthesis intermediate, wherein the carbonyl cyanoimine skeleton exhibits various reaction activities, such that the beta-carbonyl-(alpha-cyanoimine) compound can be converted into other corresponding active compounds; the raw materials used in the method are simple and easy to obtain, and t-butyl isocyanide is used as the cyano source of the reaction, and has the best reactivity and the best substrate adaptability under the promotion of silver trifluoromethanesulfonate; and the conventional reaction solvent is used during the reaction process, and the method has characteristics of simple operation, mild condition, environmental protection and general-to-excellent yield, and has good development prospect in industrial production.

Description

technical field [0001] The invention relates to a β-carbonyl-(α-cyanoimine) compound and a synthesis method thereof. Background technique [0002] β-carbonyl-(α-cyanoimine) compounds are a class of organic synthesis intermediates with application value, which can be used to rapidly construct other organic compounds with more complex and variable structures. For example, Zhao et al. synthesized a series of 2-cyano-3-arylquinoxaline compounds with β-carbonyl-(α-cyanoimine) compounds, see reference: Zhao, Y.-L. et al. Org. Biomol. Chem., 2016, 14, 165. Zarranz et al. synthesized a variety of 2-cyano-3-arylquinoxaline compounds and tested their inhibitory activity against Plasmodium falciparum strain FcB1, and the results showed that four new compounds showed higher inhibitory activity , see References: Zarranz, B. et al. Arzneim.-Forsch. (Drug Res.), 2005, 55, 754. Chloroquine is a major class of drugs for the main treatment of malaria. The study by Vicente et al. found that...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/61C07F7/10
CPCC07C253/30C07C255/61C07F7/10
Inventor 许斌赵雷阳刘秉新谭启涛王辉丁昌华
Owner SHANGHAI UNIV
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