Synthesis method of 2-amino-4H-pyran and derivative of 2-amino-4H-pyran

A synthesis method and derivative technology, applied in the field of synthesis of 2-amino-4H-pyran and its derivatives, can solve the problems of high cost, low yield, high reaction temperature, etc., and achieve the effect of increasing yield

Active Publication Date: 2019-08-09
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these synthetic methods have problems of one kind or another, such as low yield, high reaction temperature, long reaction time, use of non-recyclable catalysts and expensive solvents leading to high costs

Method used

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  • Synthesis method of 2-amino-4H-pyran and derivative of 2-amino-4H-pyran
  • Synthesis method of 2-amino-4H-pyran and derivative of 2-amino-4H-pyran
  • Synthesis method of 2-amino-4H-pyran and derivative of 2-amino-4H-pyran

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Embodiment 1

[0026] The synthetic method of 2-amino-4H-pyran of the present invention comprises: vinyl acetate, 1,3-dicarbonyl compound and malononitrile are mixed under the condition that reaction medium and catalyzer Candida rugosa lipase exist, in 2-Amino-4H-pyran and its derivatives were prepared by reacting in a constant temperature shaker at 30° C. with a rotational speed of 150 rpm for 30 minutes; wherein, the reaction medium included ethylene glycol and deionized water.

[0027] The proportioning relationship of vinyl acetate, 1,3-dicarbonyl compound, malononitrile, reaction medium and catalyst Candida rugosa lipase is: 0.2mL:0.05mmol:0.1mmol:10mL:2mg; wherein, in the reaction medium The volume ratio of ethylene glycol and deionized water is 6:4.

Embodiment 2

[0030] The 2-amino-4H-pyran method of the present invention comprises: vinyl acetate, 1,3-dicarbonyl compound and malononitrile are mixed under the condition that reaction medium and catalyzer Candida rugosa lipase exist, at 37 ℃ 1. React for 20 minutes in a constant temperature shaker with a rotating speed of 200 rpm to prepare 2-amino-4H-pyran and its derivatives; wherein, the reaction medium includes ethylene glycol and deionized water.

[0031] The proportioning relationship of vinyl acetate, 1,3-dicarbonyl compound, malononitrile, reaction medium and catalyst Candida rugosa lipase is: 0.4mL:0.1mmol:0.2mmol:10mL:5mg; wherein, in the reaction medium The volume ratio of ethylene glycol and deionized water is 7:3.

[0032] The yield of 2-amino-4H-pyran in this example is 96.8%.

Embodiment 3

[0034] The synthetic method of 2-amino-4H-pyran of the present invention comprises: vinyl acetate, 1,3-dicarbonyl compound and malononitrile are mixed under the condition that reaction medium and catalyzer Candida rugosa lipase exist, in 2-amino-4H-pyran and its derivatives were prepared by reacting in a constant temperature shaker at 50° C. and a rotation speed of 250 rpm for 15 minutes; wherein, the reaction medium included ethylene glycol and deionized water.

[0035] The proportioning relationship of vinyl acetate, 1,3-dicarbonyl compound, malononitrile, reaction medium and catalyst Candida rugosa lipase is: 0.6mL:0.2mmol:0.4mmol:10mL:10mg; wherein, in the reaction medium The volume ratio of ethylene glycol and deionized water is 8:2.

[0036] The yield of 2-amino-4H-pyran in this example is 95.4%.

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Abstract

The invention discloses a synthesis method of 2-amino-4H-pyran and a derivative of the 2-amino-4H-pyran. According to the method, candida rugosa lipase (CRL) is adopted as a catalyst to initiate a tandem MCR reaction, and 2-amino-4H-pyran is synthesized in one pot under the condition that ethanol and deionized water are adopted as reaction media, the reaction efficiency is high, few by-products are generated, and the products are environmentally friendly; the method is environmentally friendly, sustainable, simple and effective for synthesis of 2-amino-4H-pyran and the derivative of the 2-amino-4H-pyran. In addition, due to the modular characteristic of MCR and the high efficiency of a tandem procedure, various product libraries can be easily assembled by simply changing a starting material and making a production medium excellent.

Description

technical field [0001] The invention relates to the technical field of pyran synthesis, in particular to a synthesis method of 2-amino-4H-pyran and its derivatives. Background technique [0002] Pyran and its derivatives, the most popular heterocyclic skeletons, have become important research objects in the fields of natural and synthetic organic chemistry due to their simple structural complexity and important biological activities. In pyran, the 4H-pyranyl cyclized heterocyclic backbone is well distributed among naturally occurring compounds and has a wide range of biological activities, such as antitumor, antibacterial, antiviral, antispasmodic and antiallergic, many containing Drug molecules with 4H-pyran moieties have been used in the treatment of various diseases. [0003] Currently, 4H-pyranyl cyclizations are mainly used to synthesize these heterocyclic nuclei through ternary reactions of aldehyde / eosin, malononitrile, and enolized C–H activating compounds with diff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32C07D311/02
CPCC07D309/32C07D311/02
Inventor 王娜余孝其杨增杰刘艳红
Owner SICHUAN UNIV
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