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Preparation method for synthesizing indoline through idodine catalysis of amide compound

A technology of amide compound and catalyzed amide, which is applied in the direction of organic chemistry, can solve problems such as environmental pollution, difficulty in realizing industrial production, and high requirements for reaction devices, and achieve the effects of simple experimental operation, high selectivity and high yield

Active Publication Date: 2015-04-29
HUNAN UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the hydrogenation reduction method requires high temperature and high pressure, high requirements on the reaction device, and easily produces by-products; the reduction method of borohydride, the reducing agent is more expensive, the cost is higher, and it is difficult to realize industrial production; the metal-acid reduction system will produce A large amount of waste acid water also uses mercury, which is highly toxic and pollutes the environment

Method used

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  • Preparation method for synthesizing indoline through idodine catalysis of amide compound
  • Preparation method for synthesizing indoline through idodine catalysis of amide compound
  • Preparation method for synthesizing indoline through idodine catalysis of amide compound

Examples

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Effect test

preparation example 1

[0016] Add amide compound II (X=C, R 1 =H,R 2 =H,R 3 , R 4 =CH 3 ), adding iodine (2eq), potassium carbonate (2eq), di-tert-butyl peroxide (0.1eq) dropwise, and DMF 2mL dropwise, and the reaction was carried out at 100°C for 24h. After the reaction was completed, 3,3-dimethylindoline-1-carbaldehyde was obtained by column chromatography separation with a yield of 93%.

preparation example 2

[0018] Add amide compound II (X=C, R 1 =H,R 2 =CH 3 , R 3 =CH 2 OAc,R 4 =CH 3 ), adding iodine (3eq), cesium carbonate (3eq), hydrogen peroxide (10eq) dropwise, and acetonitrile 2mL dropwise, and the reaction was carried out at 80°C for 24h. After the reaction was completed, 3-methyl-3-acetate methylindoline-1-ethanone was obtained through column chromatography separation with a yield of 91%.

preparation example 3

[0020] Add amide compound II (X=C, R 1 =H,R 2 =CH 3 , R 3 , R 4 =Cy), add iodine (2eq), potassium carbonate (2eq), drop p-chlorotoluene (2eq), dropwise add acetonitrile 2mL, and react at 140°C for 5h. After the reaction was completed, 3,3-dicyclohexylindoline-1-ethanone was obtained by separation by column chromatography with a yield of 53%.

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Abstract

The invention provides an environment-friendly catalytic synthesis method for synthesizing indoline through catalysis of an amide compound. The method comprises the following steps: using the easily obtained amide compound as a raw material, using iodine as a catalyst, adding alkali, using peroxide as an oxidant, and in a polar solvent, performing reflux reaction at 80-160 DEG C, so as to obtain a corresponding indoline compound. The method is low in cost and free of heavy metal pollution; by the method, requirements on environment-friendly chemistry and sustainable development are met; a catalytic effect on a complicated substrate is relatively good, so that diversity of products is greatly enriched; the method further has the main advantages as follows: by the method, an experiment is simple and convenient, the yield is high, the applicability is wide, high efficiency, economy and environment friendliness are realized in a true sense, and the practicability is relatively high.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and specifically relates to a non-metallic iodine element as a catalyst, using amide compounds as raw materials, peroxides as oxidants, and alkalis as additives to undergo self-coupling and ring-closing reactions in organic solvents , a green catalytic synthesis method to obtain indoline derivatives in high yield. 【Background technique】 [0002] Nitrogen-containing organic compounds are an important part of organic chemistry research, and are important constituent units of some drugs; most of them contain biological activity and are commonly found in drugs. The research on benzonitrogen-containing heterocyclic compounds has always been an area of ​​interest to organic chemists. Therefore, methods for synthesizing these compounds conveniently and efficiently have attracted people's attention. [0003] Indoline is an important constituent unit of some drugs. It is a hot spot in this fi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D209/12C07D209/10C07D409/06
CPCC07D209/08C07D209/10C07D209/12C07D409/06
Inventor 邱仁华龙进国许新华李宁波朱龙志尹双凤
Owner HUNAN UNIV
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