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Aryl oxazolidinone compound of P-difluoroalkyl and preparation method thereof

A compound and alkyl technology, applied in the field of difluoroalkyl aryl oxazolidinone compounds and their preparation, can solve the problems of many steps, poor compatibility of functional groups, harsh reaction conditions, etc.

Active Publication Date: 2020-10-23
CHENGDU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The traditional method for synthesizing difluoromethylated carboxylic acid derivatives is the reductive (deoxy)fluorination of dicarbonyl compounds with SF4 or trifluorinated dialkylamines (DAST or DeoxoFluor), These synthetic routes not only have many steps but also are limited by harsh reaction conditions and poor compatibility of functional groups

Method used

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  • Aryl oxazolidinone compound of P-difluoroalkyl and preparation method thereof
  • Aryl oxazolidinone compound of P-difluoroalkyl and preparation method thereof
  • Aryl oxazolidinone compound of P-difluoroalkyl and preparation method thereof

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Experimental program
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Embodiment 1

[0097] Example 1 Synthesis of aryl oxazolidinones to difluoroalkyl

[0098]

[0099] where R 1 , R 2 The number of substituents is not limited.

[0100] Mix 0.25mmol 3-aryloxazolidinone substrate 1 and 4equiv ethyl difluorobromoacetate 2, add 10mol% catalyst, 20mol% ligand and 2equiv base to the reaction tube, add dry n-Hexane (1mL), react at 140°C for 24h to obtain a mixed liquid, add water and ethyl acetate to extract three times after the reaction, combine the organic layers, anhydrous Na 2 SO 4 The organic layer was dried, filtered, concentrated, separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate=50 / 1-1 / 1) to obtain para-difluoroalkylated aryl oxazolidinone compound 3.

[0101] According to the above method, according to the specific structural formula of the para-difluoroalkylated aryl oxazolidinone compound to be synthesized, select the corresponding aryl oxazolidinone substrate and ethyl difluorobromoacetate to react, Such as...

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Abstract

The invention discloses an aryl oxazolidinone compound of p-difluoroalkyl and a preparation method thereof. According to the invention, an oxazolinone fragment with wide biological activity is used asa guide group, aryl para-position difluoroalkylation reaction is realized through palladium catalysis, a series of para-position fluorine substituted aryl oxazolidinone derivatives are efficiently and conveniently prepared, and a foundation is laid for further drug development.

Description

technical field [0001] The invention relates to the field of p-difluoroalkyl aryl oxazolidinone compounds, in particular to a p-difluoroalkyl aryl oxazolidinone compound and a preparation method thereof. Background technique [0002] The oxazolidinone skeleton widely exists in biologically active natural products and drug molecules, such as antibacterial drugs linezolid and tedizoline, anticoagulant rivaroxaban and antidepressant drug tolofloxacin. In recent years, the synthesis and structural modification of such heterocyclic compounds have received extensive attention, and the modification of their skeleton structures is also of great significance for structural diversity. [0003] Difluoromethylene (CF 2 ), can be used as a lipophilic hydrogen bond donor to improve the membrane permeability and binding affinity of biologically active molecules, which will significantly change the physical and biological activities of molecules, so functionalized difluoromethylated arenes...

Claims

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Application Information

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IPC IPC(8): C07D263/22C07D207/27C07F7/18C07D263/20
CPCC07D263/22C07D207/27C07F7/1804C07D263/20
Inventor 马文博方新月辜玲慧李喆宇谭玉强
Owner CHENGDU UNIV
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