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Synthetic method of visible light promoted polycyclic quinazolinone compound initiated by N-hydroxyphthalimide ester decarboxylation

A technology of hydroxyphthalimide esters and polycyclic quinazolinones, which is applied in the field of organic synthesis and can solve problems such as reaction time and reaction condition limitations

Pending Publication Date: 2022-06-24
HUNAN POLICE ACAD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditionally, the synthesis of polycyclic quinazolinones often requires external catalysts for normal chemical conversion, which is limited by reaction time and reaction conditions

Method used

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  • Synthetic method of visible light promoted polycyclic quinazolinone compound initiated by N-hydroxyphthalimide ester decarboxylation
  • Synthetic method of visible light promoted polycyclic quinazolinone compound initiated by N-hydroxyphthalimide ester decarboxylation
  • Synthetic method of visible light promoted polycyclic quinazolinone compound initiated by N-hydroxyphthalimide ester decarboxylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] The quinazolinone compound represented by formula 1a (40.0 mg, 0.2 mmol), the N-hydroxyphthalimide ester compound represented by formula 2a (14.8 mg, 0.3 mmol), Potassium iodide (KI, 49.8mg, 1.5equiv), triphenylphosphine (PPh 3 , 5.2mg, 10mol%) and DMSO / H 2 O (1.0 mL / 1.0 mL), then the reactor was stirred and reacted under nitrogen atmosphere and 18W blue LED light, and the reaction progress was monitored by TLC until the raw materials disappeared (the reaction time was 24 hours). After the reaction was completed, the reaction solution was reduced to The solvent was concentrated under pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane = 5:1) to obtain the target product (72% yield). The structural formula of the product is shown in formula I-1. The data is: 1 H NMR (500MHz, CDCl 3 )δ: 8.28(d, J=8.0, 1H), 7.73-7.69(m, 2H), 7.45-7.42(m, 1H), 4.33-4.29(m, 1H), 3.96-3.91(m, 1H), 3.25...

Embodiment 2

[0018] Sodium iodide was used instead of potassium iodide, and other conditions were the same as in Example 1, and the yield of the target product I-1 was 65%.

Embodiment 3

[0020] The potassium iodide was replaced with lithium iodide, and other conditions were the same as those in Example 1, and the yield of the target product I-1 was 42%.

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Abstract

The invention relates to a synthetic method of a polycyclic quinazolinone compound initiated by N-hydroxyphthalimide ester decarboxylation promoted by visible light. The method comprises the following steps: in a nitrogen atmosphere, putting a quinazolinone compound, an N-hydroxyphthalimide ester compound, an iodine additive and a ligand into a solvent, and synthesizing the polycyclic quinazolinone product through oxidative decarboxylation and free radical cyclization reaction under the driving of visible light. The method is high in yield, has the advantages of being wide in substrate application range, mild in reaction condition, economical, environment-friendly, green and efficient, and is particularly suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, relates to the synthesis of polycyclic quinazolinone compounds, and in particular relates to a visible light-promoted N-hydroxyphthalimide ester decarboxylation induced polycyclic quinazolinone compound in the absence of A transition metal catalyst, a cyclization reaction method in an aqueous system. Background technique [0002] Solvents are used in most chemical reactions and are the focus of green chemistry. Traditionally widely used organic solvents are volatile, toxic and flammable, which may pose a major safety hazard. In contrast, water has the advantages of safety, environmental protection, low cost, and non-combustibility, and is considered as an ideal solvent for organic synthesis, so it has received extensive attention. In addition to solvents, catalysts are also the focus of green chemistry, and metal-free catalyst strategies open a new journey for synthetic chemistry. The use of m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D471/04
CPCC07D487/04C07D471/04
Inventor 易荣楠黄娟娟陈瑶清谈旺冯嘉琦汪楚力刘曦辛翠贺江南
Owner HUNAN POLICE ACAD
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