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Synthetic method of 2-alkyl substituted chromanone compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of unobtainable raw materials, cumbersome reaction operations, and waste generation, and achieve the effects of high alkyl diversity, high reaction yield, and wide sources.

Active Publication Date: 2018-08-17
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The characteristics are that the raw materials are not easy to obtain, the reaction operation is cumbersome, waste will be generated, and metal residues are difficult to remove, etc.
Recently, an alkylation method using simple alkanes as alkyl sources has been developed [Narayan, R.; Antonchick, A.P. Chem.-Eur. J. 2014, 20, 4568; Zhao, J.; Fang, H.; Qian ,P.; Han,J.; Pan,Y.Org.Lett.2014,16,5342], but the disadvantage is that the alkyl group is limited to cycloalkyl groups with higher symmetry

Method used

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  • Synthetic method of 2-alkyl substituted chromanone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Under nitrogen protection, chromone 1a (0.2 mmol), pivalaldehyde 2a (0.8 mmol), di-tert-butyl peroxide (DTBP, 0.6 mmol), and isopropanol (1 mL) were added to a Schlenk reaction tube and sealed. Heating to 120°C, the reaction time was 12 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3aa was obtained through column chromatography. The conversion of chromone 1a was 94%, and the yield of 2-tert-butylchromanone 3aa was 81%. 1 H NMR (CDCl 3 ,400MHz):δ7.85(dd,J=8.1,1.8Hz,1H),7.47-7.42(m,1H),6.99-6.95(m,2H),4.04(dd,J=12.6,4.1Hz,1H ), 2.72-2.61(m,2H), 1.05(s,9H).

Embodiment 2

[0016] Under nitrogen protection, 6-methylchromone 2b (0.2 mmol), pivalaldehyde 2a (0.8 mmol), tert-butyl hydroperoxide (TBHP, 0.6 mmol), isopropanol (1 mL) were added to a Schlenk reaction tube In, sealed. Heating to 120°C, the reaction time was 12 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3ba was obtained through column chromatography. The conversion of chromone 2b was 92%, and the yield of 6-methyl-2-tert-butylchromanone 3ba was 88%. 1 H NMR (CDCl3, 400MHz): δ7.61 (d, J = 1.6Hz, 1H), 7.23 (dd, J = 8.4, 2.2Hz, 1H), 6.84 (d, J = 8.4Hz, 1H), 4.03- 3.91 (m, 1H), 2.67-2.56 (m, 2H), 2.26 (s, 3H), 1.02 (s, 9H).

Embodiment 3

[0018] Under nitrogen protection, add 7-methoxychromone 2c (0.2 mmol), pivalaldehyde 2a (0.8 mmol), di-tert-butyl peroxide (DTBP, 0.6 mmol), isopropanol (1 mL) into a Schlenk reaction tube In, sealed. Heating to 120°C, the reaction time was 12 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3ca was obtained through column chromatography. The conversion of chromone 2c was 100%, and the yield of 2-tert-butyl-7-methoxychromanone 3ca was 98%. 1 H NMR (CDCl 3 ,400MHz): δ7.73(d,J=8.8Hz,1H),6.49(dd,J=8.8,2.2Hz,1H),6.36(d,J=2.3Hz,1H),4.00-3.96(m, 1H), 3.77(s, 3H), 2.62-2.48(m, 2H), 1.00(s, 9H).

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Abstract

The invention relates to a method to simply and efficiently prepare a 2-alkyl substituted chromanone compound and relates to the field of medicine, organic chemical industry and fine chemical industry. The method uses chromone compounds and fatty aldehyde compounds as materials, and the 2-alkyl substituted chromanone compound is synthesized in the presence of the free radical initiators. The reaction conditions include: heating to 100-150 DEG C for 10-15 hours; isopropanol, tertiary butanol, chlorobenzene, acetonitrile, dimethyl sulfoxide and acetone are used as reaction solvents; tert-butyl hydroperoxide, tert-butyl peroxybenzoate, hydrogen peroxide, dicumyl peroxide and benzoyl peroxide are used as free radical initiators. Simple post-treatment can be performed after the reaction so as to obtain a series of 2-primary, secondary or tertiary alkyl substituted chromanone compounds.

Description

technical field [0001] The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a simple and efficient synthesis of 2-alkyl substituted chroman by using fatty aldehyde as an alkylating agent without the participation of metals and under the action of a free radical initiator The ketone method. Background technique [0002] Molecules with chromone or chromanone skeleton structures are widely found in natural products and drug molecules, and many of them are physiologically active, playing an important role in the fields of anticancer, antimalarial, antibacterial, antioxidative and antiinflammatory. important role. Undoubtedly, further modifications to the skeleton structure of chromone or chromanone will result in a series of prodrug molecular libraries with biological activity and potential drug activity. Alkyl substitution can significantly improve the solubility and pharmacokinetic activity of organic molecul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
Inventor 于金涛陈荣真孙松成江
Owner CHANGZHOU UNIV
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