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Eight-membered nitrogen-oxygen heterocyclic spiro indolone compound and preparation method thereof

A technology for heterocyclic spiro indolones and compounds is applied in the field of compound preparation, can solve rare problems and the like, and achieves the effects of short time, mild reaction conditions and simple operation

Active Publication Date: 2018-11-23
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the spiro indolinones reported in the literature contain 3-6 membered spiro heterocyclic ring systems; in contrast, the reports of spiro indolinones containing medium-sized spiro heterocyclic structural units are still very rare

Method used

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  • Eight-membered nitrogen-oxygen heterocyclic spiro indolone compound and preparation method thereof
  • Eight-membered nitrogen-oxygen heterocyclic spiro indolone compound and preparation method thereof
  • Eight-membered nitrogen-oxygen heterocyclic spiro indolone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Weigh 1b (22.0mg, 0.1mmol), 2a (24.2mg, 0.1mmol), palladium catalyst (2.89mg, 0.0025mmol) and ligand PPh 3 (2.6mg, 0.01mmol) was dissolved in 1mL of tetrahydrofuran, added DBU (29.8μL, 0.2mmol) and stirred for 2 hours (detect the reaction with TLC), after the reaction was complete, the crude product was subjected to column chromatography (the eluent was selected as volume ratio of 8:1 petroleum ether / ethyl acetate mixed solution) to obtain the target product trans-3ba (11.7mg), with a yield of 28%; cis-3ba (9.6mg), with a yield of 23%.

[0038] Characterization and analysis of target objects:

[0039] trans-3ba: yellow solid, 1 H NMR (400MHz, CDCl 3 ):δ7.48-7.44(m,2H),7.34(td,J=7.8,1Hz,1H),7.18(d,J=7.2Hz,1H),7.04(t,J=7.48Hz,1H), 6.94-6.90(m, 2H), 6.87(d, J=7.8Hz, 1H), 6.23(t, J=8.5Hz, 1H), 5.70-5.64(m, 1H), 4.76(d, J=13.6Hz ,1H),4.63(d,J=13.6Hz,1H),3.84(s,3H),3.22(s,3H),3.02(s,1H),2.53(s,1H),2.45(d,J= 10.2Hz,1H)ppm; HRMS(ESI)m / z:C 22 h 21 f 3 N 2 o ...

Embodiment 2

[0042]

[0043]Weigh 1c (26.8mg, 0.1mmol), 2c (24.2mg, 0.1mmol), palladium catalyst (2.89mg, 0.0025mmol) and ligand PPh 3 (2.6mg, 0.01mmol) was dissolved in 1mL of tetrahydrofuran, added DBU (29.8μL, 0.2mmol) and stirred for 2 hours (detect the reaction with TLC), after the reaction was complete, the crude product was subjected to column chromatography (the eluent was selected as volume The ratio of 8:1 petroleum ether / ethyl acetate mixed solution) can obtain the target product trans-3ca (11.3mg), the yield is 24%; cis-3ca (11.3mg), the yield is 24%.

[0044] Characterization and analysis of target objects:

[0045] trans-3ca: white solid, 1 H NMR (400MHz, CDCl 3 ):δ7.53-7.49(m,2H),7.40-7.37(m,2H),7.34(dd,J=7.7,1.2Hz,1H),7.15(d,J=7.2Hz,1H),7.05( t,J=7.2Hz,1H),6.88(d,J=7.8Hz,1H),6.32(t,J=8.5Hz,1H),5.68-5.62(m,1H),4.76(d,J=13.5 Hz, 1H), 4.60(d, J=13.5, 1H), 3.22(s, 3H), 2.97(s, 1H), 2.57(s, 1H), 2.44(d, J=10.2Hz, 1H)ppm; HRMS(ESI)m / z:C 21 h 18 BrF 3 N 2 o 2 [M+H] +...

Embodiment 3

[0048]

[0049] Weigh 1d (22.4mg, 0.1mmol), 2d (24.2mg, 0.1mmol), palladium catalyst (2.89mg, 0.0025mmol) and ligand PPh 3 (2.6mg, 0.01mmol) was dissolved in 1mL of tetrahydrofuran, added DBU (29.8μL, 0.2mmol) and stirred for 2 hours (detect the reaction with TLC), after the reaction was complete, the crude product was subjected to column chromatography (the eluent was selected as volume The ratio of 8:1 petroleum ether / ethyl acetate mixed solution) can obtain the target product trans-3da (14.5mg), the yield is 34%; cis-3da (13.6mg), the yield is 32%.

[0050] Characterization and analysis of target objects:

[0051] trans-3da: yellow solid, 1 H NMR (400MHz, CDCl 3 ):δ7.47-7.43(m,2H),7.37-7.33(m,3H),7.15(d,J=7.2Hz,1H),7.05(t,J=7.2Hz,1H),6.88(d, J=7.8Hz, 1H), 6.31(t, J=8.5Hz, 1H), 5.68-5.62(m, 1H), 4.77(d, J=13.5Hz, 1H), 4.61(d, J=13.5Hz, 1H), 3.22(s, 3H), 2.98(s, 1H), 2.58(s, 1H), 2.45(d, J=10.2Hz, 1H) ppm; HRMS(ESI) m / z: C 21 h 18 CIF 3 N 2 o 2 [M+H] + The theore...

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Abstract

The invention discloses an eight-membered nitrogen-oxygen heterocyclic spiro indolone compound and a preparation method thereof, and belong to the technical field of preparation of compounds. The method specifically comprises the following steps that vinyl ethylene carbonate and trifluoroethyl substituted isatin-3-imine serve as synthetic materials, a metal palladium catalyst, a phosphorus-contained ligand and an acid-base additive are added, and reaction is carried out at room temperature so as to obtain a product. The preparation method has the advantages of being mild in reaction conditions, high in reaction speed, simple in post-treatment and wide in application range and is a brand-new method for efficiently synthesizing the eight-membered nitrogen-oxygen heterocyclic spiro indolone compound with the potential bioactivity.

Description

technical field [0001] The invention specifically relates to a method for preparing an eight-membered nitrogen-oxyheterocyclic spiroindolinone, which belongs to the technical field of compound preparation. Background technique [0002] Spiroindolinone is a natural alkaloid with a unique chemical structure. It has an advantageous drug skeleton structure and strong drug-like properties. It has extensive and important biological activities and medicinal values, such as anti-cancer, anti-HIV, anti-tuberculosis and Biological activity such as anti-malarial. At present, most of the spiro indolinones reported in the literature contain 3-6 membered spiro heterocyclic ring systems; in contrast, the reports of spiro indolinones containing medium-sized spiro heterocyclic structural units are still very rare. Therefore, the construction of an efficient and concise cycloaddition reaction to synthesize spiroindolinones containing medium-sized spiroheterocyclic structural fragments is of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10
CPCC07D498/10
Inventor 赵洪武王立茹郭家明丁晚秋杜娟冯宁宁
Owner BEIJING UNIV OF TECH
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