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Chromane bridged-ring isoindolinone and preparation method thereof

A technology of isoindolinone and bridged ring, which is applied in the field of chroman bridged ring isoindolinone and its preparation, and achieves the effects of mild reaction conditions, high yield and easy separation

Active Publication Date: 2018-12-07
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the structural modification of the isoindolinone core mainly focuses on the alkylation reaction (Tetrahedron, 2017, 73, 819.), the cyclization series reaction (Tetrahedron Lett., 2015, 21, 2787.) and the spirocyclization reaction (Tetrahedron , 2008,64,3505.), the molecules constructed by these reactions either only newly build a single ring to form a ring structure on the basis of isoindolinone, or are simply alkylated, and in the isoindolinone ketone skeleton There is no report on the construction of bridge rings on the basis of

Method used

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  • Chromane bridged-ring isoindolinone and preparation method thereof
  • Chromane bridged-ring isoindolinone and preparation method thereof
  • Chromane bridged-ring isoindolinone and preparation method thereof

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Embodiment 1

[0025] Preparation of chroman-bridged isoindolinone 3a: Into a 10mL hard glass reaction tube, add isoindolinone 1a (0.22mmol, 45.2mg), o-hydroxychalcone 2a (0.20mmol, 44.9mg), for Toluenesulfonic acid (6.9 mg, 0.04 mmol) was added, then 1 mL of acetonitrile was added, and the mixture was stirred at 35° C. for 24 h. After the reaction was complete, it was filtered, and the filter cake was the target compound 3a (white solid, yield 97%).

[0026] The obtained compound 3a proton nuclear magnetic resonance spectrum, carbon spectrum, infrared and high resolution mass spectrometry data are as follows:

[0027] 1 H NMR (400MHz, CDCl 3 ), δ7.94(d, J=8.0Hz, 2H), 7.63(d, J=8.0Hz, 1H), 7.58(d, J=8.0Hz, 1H), 7.51-7.45(m, 3H), 7.43 -7.39(m, 1H), 7.33(t, J=8.0Hz, 1H), 6.98(t, J=8.0Hz, 1H), 6.87(d, J=8.0Hz, 1H), 6.84(d, J= 8.0Hz,1H),6.63(t,J=8.0Hz,1H),4.35-4.29(m,1H),4.22-4.16(m,1H),4.09(s,1H),2.71-2.63(m,2H ),1.29(t,J=8.0Hz,3H); 13 CNMR (100MHz, CDCl 3 )δ 170.9, 169.6, 152.2, 141.8, ...

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Abstract

The invention discloses a chromane bridged-ring isoindolinone and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the followingsteps: adding isoindolinone and o-hydroxychalone to acetonitrile solvent, and carrying out a Michael addition / condensation / cyclization tandem reaction with p-toluene sulfonic acid as a catalyst at 35DEG C to prepare the chromane bridged-ring isoindolinone. According to the preparation method, intermediate separation is avoided, and pure products can be obtained through filtration or column chromatography. The preparation method has the advantages of mild reaction conditions, simple operation, wide substrate range and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a chroman-bridged ring isoindolinone and a preparation method thereof. Background technique [0002] Isoindolinone is the core skeleton of many natural products and drugs, and has important physiological activities. Therefore, it is of great theoretical significance and practical value to develop an efficient method for synthesizing isoindolinone or to chemically modify the isoindolinone core. Carrying out research in this area not only enriches the types of isoindolinones, but also provides more candidate molecules for drug screening. At present, the structural modification of the isoindolinone core mainly focuses on the alkylation reaction (Tetrahedron, 2017, 73, 819.), the cyclization series reaction (Tetrahedron Lett., 2015, 21, 2787.) and the spirocyclization reaction (Tetrahedron , 2008,64,3505.), the molecules constructed by these reactions either only newly ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/18
Inventor 王琪琳靳少静徐括喜卜站伟
Owner HENAN UNIVERSITY
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