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Preparation method of alkane C (sp3)-H functionalization started polycyclic quinazolinone derivative in water phase

The technology of polycyclic quinazolinone and quinazolinone is applied in the field of preparation of polycyclic quinazolinone derivatives initiated by C-H functionalization of alkanes in aqueous phase, and can solve the problems of lengthy reaction procedures, complicated preparation of raw materials, Complex reaction conditions and other problems, to achieve a wide range of effects

Pending Publication Date: 2022-07-12
HUNAN POLICE ACAD
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, these preparation methods have disadvantages such as complex reaction conditions, complicated raw material preparation and lengthy reaction procedures.

Method used

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  • Preparation method of alkane C (sp3)-H functionalization started polycyclic quinazolinone derivative in water phase
  • Preparation method of alkane C (sp3)-H functionalization started polycyclic quinazolinone derivative in water phase
  • Preparation method of alkane C (sp3)-H functionalization started polycyclic quinazolinone derivative in water phase

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] 40.0 mg (0.2 mmol) of the quinazolinone compound represented by formula 1a, 0.2 mL of cyclohexane represented by formula 2a, 58.5 mg (2.0 equiv) of di-tert-butyl peroxide, and 58.5 mg (2.0 equiv) of di-tert-butyl peroxide were added to the Schlenk reaction flask. 11.5 mg (0.2 equiv) of sodium alkyl sulfonate and 1.8 mL of water, then the reaction flask was stirred and reacted at 95° C. The reaction progress was monitored by TLC until the raw materials disappeared (the reaction time was 28 hours). After the reaction stopped, the reaction solution was extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / normal Hexane=7:1) to obtain the target product (yield 87%), the product structural formula is shown in formula I-1, and the characterization data are: 1 H NMR (400MHz,...

Embodiment 2

[0018] The oxidant used tert-butyl peroxide (TBHP) instead of di-tert-butyl peroxide (DTBP), and other conditions were the same as in Example 1, and the yield of the target product I-1 was 71%.

Embodiment 3

[0020] The oxidizing agent used benzoyl peroxide (BPO) instead of di-tert-butyl hydroperoxide (DTBP), and other conditions were the same as those in Example 1, and the yield of the target product I-1 was 58%.

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Abstract

The invention relates to a preparation method of a polycyclic quinazolinone derivative started by alkane C (sp3)-H functionalization in a water phase, in particular to a novel method for effectively synthesizing polycyclic quinazolinone by carrying out C (sp3)-H functionalization on alkane to generate alkyl free radicals and then cyclizing the free radicals of olefin substituted quinazolinone. Adding the raw materials, namely a quinazolinone compound, alkane, a phase transfer agent and an oxidizing agent into a solvent in an air atmosphere, and stirring at a certain reaction temperature to react, so as to generate the polycyclic quinazolinone derivative. The method has the advantages of wide application range of reaction substrates, greenness and high efficiency, and is particularly suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to an alkane C(sp 3 )–H functionalization-initiated preparation of polycyclic quinazolinone derivatives. Background technique [0002] The synthesis of polycyclic quinazolinones is a core step in the preparation of natural products with pharmaceutical and biological activities. In addition, the molecular skeleton itself has medicinal properties such as anti-depression, anti-asthma, and anti-infection. Generally, there are many synthetic methods for polycyclic quinazolinones, mainly including: 1) reductive cyclization reaction of complex aryl azides, 2) cyclization reaction of anthranilic acid, 3) intramolecular reaction of primary alcohols Photocatalytic reaction, 4) Conversion reaction of N-cyanamide olefin. However, these preparation methods have disadvantages such as complicated reaction conditions, complicated preparation of raw materials and lengthy reaction procedures. Recen...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 易荣楠陈瑶清黄娟娟唐钰强胡润楷肖大中夏婵娟卜芃
Owner HUNAN POLICE ACAD
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