Synthesis method for cinnoline salt compound

A technology of cinnoline salt compound and synthesis method, which is applied in the field of synthesis of cinnoline salt compound, can solve problems such as reduced practicality, and achieve the effects of good product yield, good research value and application potential

Active Publication Date: 2021-03-26
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, in many cases, these methods require the use of large quantities of strong oxidizing agents, expensive additives, and noble metal catalysts, which greatly reduces the practicability of these methods

Method used

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  • Synthesis method for cinnoline salt compound
  • Synthesis method for cinnoline salt compound
  • Synthesis method for cinnoline salt compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 2,3-Diphenyl-4-oxocinnoline ylide

[0023]

[0024] 2-Phenylethynylaniline (96.6 mg, 0.5 mmol), nitrosobenzene (80.3 mg, 0.75 mmol), CuCl (5.0 mg, 0.05 mmol), 4-dimethylaminopyridine ( 24.4mg, 0.2mmol), toluene (1.5mL), and then seal the tube. Put the reaction mixture into an oil bath at 100°C and stir for 24 hours, take it out and cool it to room temperature, transfer the original reaction solution, add an appropriate amount of ethyl acetate to wash, mix the original solution with the washing solution, concentrate under reduced pressure and adsorb on silica gel, and then directly carry out Silica gel chromatographic separation, using a mixture of dichloromethane and ethyl acetate at a volume ratio of 50:1 as the eluent, was obtained after column chromatography with a yield of 74%. 1 H-NMR (500MHz, DMSO): δ8.25(d, J=8.0Hz, 1H), 7.95(d, J=8.5Hz, 1H), 7.88(t, J=6.5Hz, 1H), 7.65(t ,J=7.0Hz,1H),7.58-7.57(m,2H),7.40(t,J=3.5Hz,3H),7.35(d,J=7.5Hz,2H),7.30-7.26(...

Embodiment 2

[0025] Example 2: 2-phenyl-3-(4-(methoxycarbonyl)phenyl)-4-oxocinnoline ylide

[0026]

[0027] Add 4-((2-aminophenyl)ethynyl)methyl benzoate (125.6mg, 0.5mmol), nitrosobenzene (80.3mg, 0.75mmol), CuCl (5.0mg, 0.05mmol), 4-dimethylaminopyridine (24.4mg, 0.2mmol), toluene (1.5mL), and then seal the tube. Put the reaction mixture in an oil bath at 100°C and stir for 24 hours, take it out and cool it to room temperature, transfer the original reaction solution, add an appropriate amount of ethyl acetate to wash, mix the original solution and washing solution, concentrate under reduced pressure and adsorb on silica gel, and carry out directly Silica gel chromatographic separation, using a mixture of dichloromethane and ethyl acetate at a volume ratio of 50:1 as the eluent, obtained after column chromatography with a yield of 86%. 1 H-NMR (500MHz, CDCl 3 ): δ8.42(d, J=8.0Hz, 1H), 7.91(d, J=8.0Hz, 3H), 7.76(t, J=8.0Hz, 1H), 7.58(t, J=7.5Hz, 1H ),7.35(d,J=9.5Hz,7H),3.87(s,3H). ...

Embodiment 3

[0028] Example 3: 2,3-diphenyl-4-oxo-7-chlorocinnoline ylide

[0029]

[0030] 5-Chloro-2-(phenylethynyl)aniline (113.8mg, 0.5mmol), nitrosobenzene (80.3mg, 0.75mmol), CuCl (5.0mg, 0.05mmol), 4 - Dimethylaminopyridine (24.4 mg, 0.2 mmol), toluene (1.5 mL). Then, seal the tube. Put the reaction mixture in an oil bath at 100°C and stir for 24 hours, take it out and cool it to room temperature, transfer the original reaction solution, add an appropriate amount of ethyl acetate to wash, mix the original solution and washing solution, concentrate under reduced pressure and adsorb on silica gel, and carry out directly Silica gel chromatographic separation, using a mixture of dichloromethane and ethyl acetate at a volume ratio of 50:1 as the eluent, was obtained after column chromatography with a yield of 73%. 1 H-NMR (500MHz, CDCl 3 ): δ8.18(d, J=9.0Hz, 1H), 7.76(d, J=1.5Hz, 1H), 7.36(dd, J=8.5Hz, J=2.0Hz, 1H), 7.27-7.24(m ,5H),7.18-7.15(m,5H). 13 C-NMR (500MHz, CDCl 3 ): δ...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method for a cinnoline salt compound. The synthesis method comprises the following step: carrying out a catalytic cyclization reaction on a compound as shown in a formula (I) and a compound as shown in a formula (II) under the action of a composite catalysis system comprising a metal catalystand assistants so as to obtain the cinnoline salt compound as shown in a formula (III). The invention provides a synthesis method of a nitrogen-containing inner salt structure. According to the synthesis method, target products with good yield can be obtained through a unique composite catalytic system and the mutual cooperation and promotion effect of components and conditions; a brand new method is provided for the synthesis of nitrogen-containing inner salt compounds; and the corresponding products have certain optical properties, and present good research value and application potential.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of a cinnoline salt compound. Background technique [0002] Quaternary ammonium salts are a class of widely used compounds that have drawn more and more attention because of their reactivity and biological activity. Among them, the cinnoline salt structure often appears in some biologically active compounds, drug molecules, alkaloids, receptors and inhibitors. [0003] In the existing synthetic research of cinnoline salt compounds, the most commonly used method is to utilize the S of cinnoline and haloalkane N 2 reaction, but this method is not suitable for nitrogen-containing heterocyclic compounds that are very valuable. [0004] Transition metal-catalyzed C–H functionalization and cross-coupling reactions have attracted extensive attention due to their advantages in atom economy and steps. Azobenzene is a widely used compound, which ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/28C07D409/04
CPCC07D237/28C07D409/04
Inventor 余小春方晓岚王舜金辉乐李俊
Owner WENZHOU UNIVERSITY
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