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Dendritic 1, 4-diene amide derivative and synthesis method thereof

A dienamide and synthesis method technology, applied in organic chemistry methods, organic chemistry, etc., can solve problems such as unreported methods, and achieve the effects of simple operation, high reaction yield, wide application prospects and economic value

Active Publication Date: 2019-12-31
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] These literatures have synthesized a series of stereospecific 1,3- and 1,4-diene compounds, but they are limited to conjugated alkenyl amides and electron-deficient alkenes as substrates, and can only activate the ortho-position of the amide group. Alkenyl carbon-hydrogen bonds, resulting in linear coupling products
The alkenylation coupling reaction of non-conjugated alkenyl amides, the method of synthesizing amide-substituted branched conjugated diene derivatives has not been reported

Method used

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  • Dendritic 1, 4-diene amide derivative and synthesis method thereof
  • Dendritic 1, 4-diene amide derivative and synthesis method thereof
  • Dendritic 1, 4-diene amide derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of (E)-4-benzylidene-N-(quinolin-8-yl)hept-6-enamide

[0043] A screw cap vial was charged with palladium acetate (4.5 mg, 0.02 mmol), dimethylsulfoxide (0.35 mL) and methanol (0.7 mL). Then, pivalic acid (20.4mg, 0.2mmol), (Z)-5-phenyl-N-(quinolin-8-yl)pent-4-enamide (30.2mg, 0.1mmol) and Allyl methyl carbonate (46.4 mg, 0.4 mmol). The vial was sealed under argon and heated to 40°C and stirred for 16 hours. After cooling, the mixture was directly applied to flash column chromatography (PE / EA=4 / 1), and the reaction solution was separated by direct column chromatography to obtain the target product as a white liquid (25.3 mg, yield 74%). The reaction formula is as follows:

[0044]

[0045] The nuclear magnetic spectrum characterization result of this reaction product is as follows: 1 H NMR (500MHz, CDCl 3 ): δ9.77(s,1H), 8.77–8.74(m,2H), 8.11(dd,J=8.5,2.0Hz,1H),7.52–7.45(m,2H),7.41(dd,J=8.5 ,4.0Hz,1H),7.30–7.24(m,4H),7.18–7.15(m,1H),6.39(s,1H),5.96–5...

Embodiment 2

[0048] Preparation of (E)-4-(4-fluorobenzylidene)-N-(quinolin-8-yl)hept-6-enamide

[0049] A screw cap vial was charged with palladium acetate (4.5 mg, 0.02 mmol), dimethylsulfoxide (0.35 mL) and methanol (0.7 mL). Then, pivalic acid (20.4 mg, 0.2 mmol), (Z)-5-(4-fluorophenyl)-N-(quinolin-8-yl)pent-4-enamide (32.0 mg , 0.1 mmol) and allyl methcarbonate (46.4 mg, 0.4 mmol). The vial was sealed under argon and heated to 40°C and stirred for 16 hours. After cooling, the mixture was directly applied to flash column chromatography (PE / EA=4 / 1), and the reaction solution was separated by direct column chromatography to obtain the target product yellow liquid (33.4 mg, yield 93%). The reaction formula is as follows:

[0050]

[0051] The nuclear magnetic spectrum characterization result of this reaction product is as follows: 1 H NMR (500MHz, CDCl 3 )δ9.76(s,1H),8.77–8.74(m,2H),8.13(dd,J=8.0,1.5Hz,1H),7.53–7.47(m,2H),7.43(dd,J=8.0, 4.0Hz, 1H), 7.20(q, J=5.5Hz, 2H), 6.96(t, J=9...

Embodiment 3

[0053] Preparation of (E)-4-(4-methoxybenzylidene)-N-(quinolin-8-yl)hept-6-enamide

[0054] A screw cap vial was charged with palladium acetate (4.5 mg, 0.02 mmol), dimethylsulfoxide (0.35 mL) and methanol (0.7 mL). Then, pivalic acid (20.4 mg, 0.2 mmol), (Z)-5-(4-methoxyphenyl)-N-(quinolin-8-yl)pent-4-enamide ( 33.2 mg, 0.1 mmol) and allyl methcarbonate (46.4 mg, 0.4 mmol). The vial was sealed under argon and heated to 40°C and stirred for 16 hours. After cooling, the mixture was directly applied to flash column chromatography (PE / EA=4 / 1). The reaction solution was separated by direct column chromatography to obtain a yellow liquid (28.0mg, yield 76%), the reaction formula is as follows:

[0055]

[0056] The nuclear magnetic spectrum characterization result of this reaction product is as follows:. 1 H NMR (500MHz, CDCl 3)δ9.79(s,1H),8.79–8.75(m,2H),8.15(dd,J=8.5,1.5Hz,1H),7.54–7.48(m,2H),7.44(dd,J=8.5, 4.5Hz, 1H), 7.20(d, J=9.0Hz, 2H), 6.84–6.82(m, 2H), 6.33(s, 1H),...

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Abstract

The invention discloses a dendritic 1, 4-diene amide derivative shown as formula (1) and a synthesis method thereof. The specific synthesis method includes: placing an alkenyl quinoline amide compound, an allyl methyl carbonate derivative, a transition metal salt catalyst and an additive in an organic solvent, carrying out heating reaction in an argon atmosphere, and carrying out aftertreatment onthe reaction liquid at the end of the reaction to obtain the dendritic 1, 4-diene amide derivative. Under mild conditions, the method provided by the invention utilizes 8-aminoquinoline amide as N, N-double coordinated guide group, takes allyl methyl carbonate as the alkenylation reagent, and efficiently realizes hydrocarbon alkenylation reaction of alkenyl and carbon site, the obtained productsare all brand new compounds, the reaction substrate has wide application range, the raw materials are economical and easily available, no exogenous oxidant is needed, the operation is simple, and thehighest yield can reach 93%, therefore the method has wide application prospect and economic value.

Description

technical field [0001] The invention relates to the technical field of synthesis of non-conjugated diene compounds, in particular to a branched 1,4-dienamide derivative and a synthesis method thereof. Background technique [0002] As we all know, the diene structure is a common chemical structure, which widely exists in natural products and pharmaceutical bioactive molecules, such as risstatin, biserin and bilolide, etc. 1,4-Dienes are also widely used as ligands in transition metal-catalyzed reactions. A variety of methods for the preparation of 1,4-diene compounds have been reported, including: catalytic coupling reaction, ene reaction, alkenylation reaction and Morita–Baylis–Hillman (Morita-Baylis-Hillman) reaction, etc. With the depletion of energy and the increasingly severe environmental problems, it is particularly urgent to develop efficient and highly selective synthesis methods of 1,4-diene compounds. [0003] The direct hydrocarbon allylation reaction of alkenes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/40C07D405/12C07D409/12C07D401/12C07B37/00
CPCC07B37/00C07D215/40C07D401/12C07D405/12C07D409/12
Inventor 钟国富张坚沈聪卢秀男丁丽媛
Owner HANGZHOU NORMAL UNIVERSITY
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