Preparation method of N-heterocyclic oxazolidine-2-ketone compound

A technology of heterocyclic oxazolidine and ketone compounds, which is applied in the field of preparation of N-heterocyclic oxazolidin-2-one compounds, can solve the problems of high cost, troublesome post-processing, complicated reaction process, etc., and achieve high The effect of universality, simple operation, high selectivity and yield

Inactive Publication Date: 2014-01-22
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It has been reported that oxazolidin-2-one and N-heterocyclic substituents are prepared by substitution reaction (Chem. Eur. J.16 (2010) 5437-5442), but this method often uses noble metal complexes and alkali metals as catalysts, The reaction process is complicated, the cost is high, and the post-processing is troublesome

Method used

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  • Preparation method of N-heterocyclic oxazolidine-2-ketone compound
  • Preparation method of N-heterocyclic oxazolidine-2-ketone compound

Examples

Experimental program
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Embodiment 1

[0023] N 2 Under protection, 2-aminopyridine 2mmol (0.19g), ethylene carbonate 10mmol (0.88g), 1-butyl-3-methylimidazolium acetate ionic liquid ([Bmim]OAc ) 0.2mmol (0.04g), heated up to 130°C and stirred for 9h, cooled to room temperature after the reaction, the product was recrystallized from ethyl acetate, and dried in vacuo to obtain a white solid 3-(2-pyridyl)oxazolidine- 2-ketone 0.31g, yield 95%.

Embodiment 2

[0025] In the preparation method of this embodiment, the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4 ), the reaction time was 12h, other preparation conditions and methods were the same as in Example 1, and 0.17g of 3-(2-pyridyl)oxazolidin-2-one was prepared with a yield of 50%.

Embodiment 3

[0027] In the preparation method of this example, the ionic liquid is 1-butyl-3-methylimidazolium bromide ([Bmim]Br), other preparation conditions and methods are the same as in Example 1, and 3-(2-pyridyl)oxa Oxazolidin-2-one 0.29g, yield 89%.

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Abstract

The invention discloses a preparation method of an N-heterocyclic oxazolidine-2-ketone compound. The preparation method comprises the following steps: mixing N-heterocyclic aromatic amine with cyclic carbonate, adding a catalytic amount of ionic liquid, and reacting to obtain the N-heterocyclic oxazolidine-2-ketone compound. By adopting the preparation method disclosed by the invention, the N-heterocyclic oxazolidine-2-ketone compound can be synthesized just by adopting a simple one-step reaction, and an additional organic solvent is not needed in the reaction process, so that the preparation method has the advantages of cleanness and high efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis methodology, and in particular relates to a preparation method of N-heterocyclic oxazolidin-2-one compounds. Background technique [0002] N-heterocyclic compounds are important intermediates in organic synthesis and have important uses in the fields of medicine (US085859) and pesticides (CN102093338). Oxazolidin-2-ones have a wide range of uses and are important in the field of medicine (Adv.Synth.Catal346(2004)954-958; Bioorg.Med.Chem9(2001)3153-3160). At the same time, it is widely used as an important intermediate in organic synthesis (Curr.Org.Synth4(2007)238-307; Curr.Org.Synth4(2007)81-135). [0003] The synthetic method of N-heterocyclic oxazolidin-2-ones is rarely reported. It has been reported that oxazolidin-2-one and N-heterocyclic substituents are prepared by substitution reaction (Chem. Eur. J.16 (2010) 5437-5442), but this method often uses noble metal complexes and alka...

Claims

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Application Information

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IPC IPC(8): C07D413/04
CPCC07D413/04
Inventor 高国华杨四娟张利锋王滨燊
Owner EAST CHINA NORMAL UNIVERSITY
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