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N-heterocyclic carbene-thiourea dual-functional-group catalyst and preparation method and application thereof

A nitrogen-heterocyclic carbene and dual-functional technology, which is applied in the field of nitrogen-heterocyclic carbene-thiourea dual-functional catalysts and its preparation, can solve the problems of limited application of bifunctional nitrogen-heterocyclic carbene asymmetric catalysis, and achieve low cost , easy to obtain raw materials, good catalytic activity effect

Active Publication Date: 2021-11-23
SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT +1
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Problems solved by technology

[0004] The purpose of this application is to provide a nitrogen-heterocyclic carbene-thiourea bifunctional catalyst and its preparation method and application, aiming to solve the existing technology of limited asymmetric catalytic application of bifunctional nitrogen-heterocyclic carbene in the non-covalent field question

Method used

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  • N-heterocyclic carbene-thiourea dual-functional-group catalyst and preparation method and application thereof
  • N-heterocyclic carbene-thiourea dual-functional-group catalyst and preparation method and application thereof
  • N-heterocyclic carbene-thiourea dual-functional-group catalyst and preparation method and application thereof

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preparation example Construction

[0042] On the other hand, the application also provides a preparation method of nitrogen heterocyclic carbene-thiourea bifunctional catalyst, such as figure 1 Shown, this preparation method comprises the steps:

[0043] S01: reacting the compound shown in formula II through nitration reaction to obtain the compound shown in formula III;

[0044] S02: the compound shown in formula III with trimethyloxonium tetrafluoroborate, Ar 2 NHNH 2 , triethyl orthoformate reaction, obtain the compound shown in formula IV;

[0045] S03: performing reductive hydrogenation reaction on the compound shown in formula IV to obtain the compound shown in formula V;

[0046] S04: the compound shown in formula V and isothiocyanate Ar 1 NCS reaction, obtains nitrogen heterocyclic carbene-thiourea bifunctional group catalyst shown in formula I;

[0047] Wherein, the structural formula of above-mentioned compound is as follows:

[0048]

[0049] Wherein, Ar1 and Ar2 are independently selected f...

Embodiment 1

[0072] A nitrogen heterocyclic carbene-thiourea bifunctional catalyst, its molecular structure is as follows:

[0073]

[0074] The preparation method of the nitrogen heterocyclic carbene-thiourea bifunctional catalyst comprises the following steps:

[0075] (1) Synthesis of intermediate ((4aR,9aS)-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2hydrogen)-one, reaction The formula and synthesis steps are as follows:

[0076]

[0077] Add 9.0g (1R,2S)-1-amino-2-indanol to 300mL tetrahydrofuran solution, cool to 0 degrees, then add 2.52g 60% sodium hydride, stir for half an hour, then add 7.1mL ethyl chloroacetate . After stirring for 4 hours, samples were taken to monitor the reaction progress (TLC detection). After the reaction was complete, the reaction system was quenched with saturated sodium bicarbonate, then extracted with ethyl acetate solution, and then the combined organic phase was dried with anhydrous sodium sulfate, and the product was obtained by recrystal...

Embodiment 2

[0092] A nitrogen heterocyclic carbene-thiourea bifunctional catalyst, its molecular structure is as follows:

[0093]

[0094] Its preparation method refers to (5aS,10bR)-9-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-2-mesitylacetone-5a,10b in Example 1 Preparation of dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate Method, except that p-nitrophenyl isothiocyanate (360 mg) was used instead of 3,5-bis(trifluoromethyl)phenyl isothiocyanate. The reaction solution was directly separated and purified by silica gel column chromatography (methanol and dichloromethane as eluents) to obtain the target product as a yellow solid.

[0095] The product VII of preparation is carried out characterizing data analysis, and its result is 1 H NMR(400MHz,DMSO)δ11.19(s,1H),10.38(s,1H),10.23(s,1H),8.16(d,J=9.1Hz,2H),7.87(s,1H),7.78 (d, J=9.1Hz, 2H), 7.41(d, J=8.0Hz, 1H), 7.25(d, J=8.0Hz, 1H), 7.15(s, 2H), 6.09(d, J=3.8Hz ,1H),5.29(d,J=16.1Hz,1H),5.17-4...

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Abstract

The invention discloses an N-heterocyclic carbene-thiourea dual-functional-group catalyst. The structural general formula of the N-heterocyclic carbene-thiourea dual-functional-group catalyst is as shown in formula I, and Ar1 and Ar2 in the formula I are independently selected from any one of aryl, substituted aryl, heteroaryl and substituted heteroaryl respectively. According to the N-heterocyclic carbene catalyst, another active site thiourea group is introduced on the basis of an N-heterocyclic carbene skeleton, multiple dual-functional thiourea N-heterocyclic carbene catalysts can be formed, and the N-heterocyclic carbene-thiourea dual-functional group catalyst has good catalytic activity in catalysis of asymmetric selena Michael reaction; therefore, the catalyst has good application in the field of organic asymmetric catalysis.

Description

technical field [0001] The application belongs to the technical field of catalytic materials, and in particular relates to a nitrogen heterocyclic carbene-thiourea bifunctional catalyst and its preparation method and application. Background technique [0002] Catalysts with dual functional groups and dual catalytic sites are often designed and successfully applied in organic asymmetric catalysis. Among them, the chiral catalyst containing thiourea group is the most widely used bifunctional catalyst, because the thiourea group in its structure can form a non-covalent bond with the substrate, resulting in good catalytic activity and stereorotation. Such as quinine thiourea catalyst. [0003] N-Heterocyclic Carbenes (NHCs) are an important class of organic small molecule catalysts. Among them, the nitrogen-heterocyclic carbene catalyst derived from the chiral aminoindanol skeleton has sprung up in recent years after the report of Professor Rovis, and has been widely used in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D498/04C07C391/00
CPCB01J31/0271C07D498/04C07C391/00B01J2231/32C07B2200/07C07C2601/08
Inventor 陈杰安黄湧李恩
Owner SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT
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