Oxygen nitrogen heterocyclic heptane derivative containing exocyclic double bond and preparation method thereof

A technology for oxazepane and derivatives is applied in the field of oxazepane derivatives and their preparation, and can solve the problems of low substrate universality, high transition metal prices, harsh reaction conditions and the like, To achieve the effects of complex and novel structure, short reaction time and simple preparation method

Pending Publication Date: 2019-06-14
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional synthetic route has problems such as harsh reaction conditions and low substrate universality.
In recent years, the synthesis of heterocyclic compounds based on transition metal-catalyzed cyclization reactions has attracted widespread attention from chemists, but the price of transition metals is high and it is easy to cause metal residues.

Method used

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  • Oxygen nitrogen heterocyclic heptane derivative containing exocyclic double bond and preparation method thereof
  • Oxygen nitrogen heterocyclic heptane derivative containing exocyclic double bond and preparation method thereof
  • Oxygen nitrogen heterocyclic heptane derivative containing exocyclic double bond and preparation method thereof

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Effect test

Embodiment 1

[0044] A kind of oxazepane derivative containing exocyclic double bond, its structural formula is:

[0045]

[0046] The preparation method of the above-mentioned oxazepane derivatives containing exocyclic double bonds comprises the following steps:

[0047] (1) With 830mmol sodium hydride as a catalyst, 200mmol diethyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press spin dry, obtain product, i.e. compound 1, structural formula

[0048] (2) Mix 80mmol of compound 1 prepared in step (1) with 200mmol of phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was ...

Embodiment 2

[0055] A kind of oxazepane derivative containing exocyclic double bond, its structural formula is:

[0056]

[0057] The preparation method of the above-mentioned oxazepane derivatives containing exocyclic double bonds comprises the following steps:

[0058] (1) With 830mmol sodium hydride as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press spin dry, obtain product, i.e. compound 1, structural formula

[0059] (2) Mix 80mmol of compound 1 prepared in step (1) with 200mmol p-fluorophenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI in anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), molar ratio

[0060] Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the ...

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PUM

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Abstract

The invention provides an oxygen nitrogen heterocyclic heptane derivative containing an exocyclic double bond and a preparation method thereof. The preparation method comprises the following steps that tetraacetylene compounds are mixed with methylbenzene toluene to perform heating reaction with 2,4,4-trimethyl-2-oxazoline, and after the reaction is finished, the mixture is naturally cooled to room temperature, and a product is purified and separated to obtain the oxygen nitrogen heterocyclic heptane derivative containing the exocyclic double bond. Compared with the prior art, the invention provides the novel preparation method of the oxygen nitrogen heterocyclic heptane derivative containing the exocyclic double bond. Compared with common heterocyclic derivatives, the oxygen nitrogen heterocyclic heptane derivative containing the exocyclic double bond has the existence of the exocyclic double bond and oxygen-nitrogen heteroatoms, and a rare seven-membered ring structure is obtained, and the structure is more complex and novel. The substance of the oxygen nitrogen heterocyclic heptane derivative containing the exocyclic double bond may further have a wide range of functions in thepharmaceutical industry, and the preparation method is simple, convenient and efficient, has short reaction time and high efficiency.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to an oxazepane derivative containing an exocyclic double bond and a preparation method thereof. Background technique [0002] Heterocyclic compounds are cyclic compounds that contain one or more heteroatoms. The number and variety of heterocyclic compounds are various, and they are an important part of organic compounds. Most of the compounds distributed in nature contain heterocyclic systems. Most heterocyclic compounds have certain physiological activity and pharmacological value, and have important applications in the fields of natural products, pharmaceutical molecules, and functional materials. [0003] The development of efficient methods for the synthesis of novel heterocyclic compounds has always been a research hotspot in synthetic organic chemistry. The traditional method of synthesizing heterocyclic compounds mainly uses the condensation reaction of carbony...

Claims

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Application Information

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IPC IPC(8): C07D267/12
Inventor 胡益民郑晓杰
Owner ANHUI NORMAL UNIV
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