Electrochemical synthesis method of trifluoromethyl-substituted polycyclic quinazolinone derivative

A polycyclic quinazolinone and trifluoromethyl technology, which is applied in the field of electrochemical synthesis of polycyclic quinazolinone derivatives, can solve the problems of large amount of three wastes, harsh reaction conditions, and less synthesis, and achieve simple operation , Raw materials are easily available, and the effect of environmental friendliness

Pending Publication Date: 2022-03-01
江苏信和生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are many synthetic methods for polycyclic quinazolinones, the synthesis of quinazolinone derivatives substituted with trifluoromethyl is less; Large amount, etc.

Method used

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  • Electrochemical synthesis method of trifluoromethyl-substituted polycyclic quinazolinone derivative
  • Electrochemical synthesis method of trifluoromethyl-substituted polycyclic quinazolinone derivative
  • Electrochemical synthesis method of trifluoromethyl-substituted polycyclic quinazolinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 6-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-11H-pyridin[2,1-b]quinazolin-11-one (I-a) preparation

[0021] Put 3-(pent-4-en-1-yl)quinazolin-4(3H)-one (II-a) (43mg, 0.2mmol) into the Shrek tube, sodium trifluoromethylsulfinate ( 94mg, 0.6mmol), p-toluenesulfonic acid (38mg, 0.2mmol), potassium hexafluorophosphate (35mg, 0.2mmol). A graphite felt anode (1.5×1×0.5 cm) and a nickel foam cathode (1.5×1 cm) were inserted in the reactor. Add dimethyl sulfoxide (4.5mL) and water (1.5mL) to form a mixed solvent, adjust the current to a constant current of 6mA, react at 60°C for 12 hours, and separate by silica gel column chromatography to obtain a white solid I-a, 42mg, m.p.143.2- 144.6°C, yield: 74%. The structural formula of I-a is:

[0022]

[0023] 1 H NMR (600MHz, CDCl 3 )δ8.22(dd, J=7.8,1.8Hz,1H),7.69(m,1H),7.59(dd,J=7.8,1.2Hz,1H),7.45–7.36(m,1H),7.31–4.27 (m,1H),3.92(dt,J=13.2,6.6Hz,1H),3.56–3.47(m,1H),3.18–3.43(m,1H),2.45–2.29(m,2H),2.07–1.94 (m,2H),...

Embodiment 2

[0024] Example 2 6-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-11H-pyridin[2,1-b]quinazolin-11-one (I-a) Preparation Put 3-(pent-4-en-1-yl)quinazolin-4(3H)-one (II-a) (43mg, 0.2mmol) and sodium trifluoromethylsulfinate into Shrek tube (94mg, 0.6mmol), benzoic acid (24mg, 0.2mmol), potassium hexafluorophosphate (35mg, 0.2mmol).

[0025] A graphite felt anode and a nickel foam cathode were inserted into the reactor. Dimethyl sulfoxide (4.5 mL) and water (1.5 mL) were added to form a mixed solvent. The current was adjusted to a constant current of 6mA, reacted at 60°C for 12 hours, and separated by silica gel column chromatography to obtain a white solid I-a, 32 mg, yield: 55%.

Embodiment 3

[0026] Example 3 6-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-11H-pyridin[2,1-b]quinazolin-11-one (I-a) preparation

[0027] Put 3-(pent-4-en-1-yl)quinazolin-4(3H)-one (II-a) (43mg, 0.2mmol) into the Shrek tube, sodium trifluoromethylsulfinate ( 94mg, 0.6mmol), acetic acid (12mg, 0.2mmol,), potassium hexafluorophosphate (35mg, 0.2mmol).

[0028] A graphite felt anode and a nickel foam cathode were inserted into the reactor. Dimethyl sulfoxide (4.5 mL) and water (1.5 mL) were added to form a mixed solvent. The current was adjusted to a constant current of 6mA, reacted at 60°C for 12 hours, and separated by silica gel column chromatography to obtain a white solid I-a, 38 mg, yield: 66%.

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Abstract

The invention relates to the technical field of electrochemical synthesis, in particular to an electrochemical synthesis method of a trifluoromethyl-substituted polycyclic quinazolinone derivative. The method comprises the following steps: sequentially adding 3-alkene alkyl substituted quinazolinone, sodium trifluoromethanesulfinate, an electrolyte, an additive and a solvent into an unseparated electrolytic cell serving as a reactor, respectively inserting a positive electrode and a negative electrode of an electrode into a reaction solution, switching on current, keeping constant current, stirring and reacting, and after the reaction is finished, performing column chromatography separation to obtain the 3-alkene alkyl substituted quinazolinone. The trifluoromethyl substituted polycyclic quinazolinone derivative is obtained. According to the method, a metal catalyst and an oxidizing agent are not needed, only electro-catalytic oxidation is used, a byproduct is hydrogen, and the method has the characteristics that raw materials are easy to obtain, operation is simple, electrolyte and a solvent can be used mechanically and the like, and has good popularization and implementation value and social and economic benefits.

Description

technical field [0001] The invention relates to the technical field of electrochemical synthesis, in particular to an electrochemical synthesis method of polycyclic quinazolinone derivatives. Background technique [0002] Quinazolinone and its derivatives are an important class of nitrogen-containing heterocyclic skeletons. Both natural products and synthetic quinazolinone derivatives have shown a wide range of pharmacological and biological activities, including antibacterial, anti-infective, anti- Inflammatory and antitumor properties. Such as natural alkaloid Mackinazolinone (Mackinazolinone), tryptanthrin (Tryptanthrin) with anti-infective effect, bronchodilator drug Vasicinone (Vasicinone), anti-inflammatory effect of Rutaecarpine (Rutaecarpine) and so on. The fluorine-containing derivatives can obviously improve the activity and reduce the cytotoxicity. In the existing synthetic derivations, the main structural modification sites are located on the benzene ring of th...

Claims

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Application Information

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IPC IPC(8): C25B3/11C25B3/28C25B11/043C25B11/031C25B11/042
CPCC25B3/11C25B3/28C25B11/043C25B11/031C25B11/042
Inventor 钟为慧刘磊凌飞
Owner 江苏信和生物医药有限公司
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