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Method for synthesizing indole[1,2-c]quinazoline compounds

A technology for quinazolines and compounds, which is applied in the field of synthesizing indole[1,2-c]quinazolines, can solve problems such as cumbersome operation steps, low yields, and restrictions on the scope of application of synthetic methods, and achieve reaction The effect of mild conditions, simple operation and wide range of substrate application

Active Publication Date: 2018-08-21
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the synthetic methods of indole[1,2-c]quinazolines have been reported in the literature, these literature methods still have many disadvantages such as unsuitable raw materials for preparation, cumbersome operation steps and low yield, which are to a large extent This restricts the scope of application of this type of synthetic method

Method used

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  • Method for synthesizing indole[1,2-c]quinazoline compounds
  • Method for synthesizing indole[1,2-c]quinazoline compounds
  • Method for synthesizing indole[1,2-c]quinazoline compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0012]

[0013] N-(2-(1H-indol-2-yl)phenyl)benzamide 1a (124.8 mg, 0.4 mmol), 1,4-dioxane (2 mL) and CuBr (5.7 mg, 0.04 mmol) was added with dilute hydrochloric acid (0.16 mL, 0.5 M, 0.08 mmol) under stirring at room temperature, and then heated and stirred at 120°C for 6 h. After the reaction was completed, saturated sodium bicarbonate was added to the reaction flask. The solution was quenched, extracted with ethyl acetate, the organic phase was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain indole[1,2-c]quinazoline 2a (85 mg, 72%) as a yellow solid. The characterization data for this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ6.34(d,J=8.4Hz,1H),6.84-6.88(m,1H),7.12(s,1H),7.18(t,J=7.6Hz,1H),7.36(td,J =1.6,7.6Hz,1H),7.41(td,J=1.6,7.6Hz,1H),7.46-7.55(m,5H),7.63(d,J=7.6Hz,1H),7.72(dd,J= 0.8,7.6Hz,1H),7.96(dd,J=0....

Embodiment 2

[0015]

[0016] According to the method described in Example 1, N-(2-(1H-indol-2-yl)phenyl)benzamide 1b (130.4 mg, 0.4 mmol), 1,4 -Dioxane (2 mL) and CuBr (5.7 mg, 0.04 mmol), dilute hydrochloric acid (0.16 mL, 0.5 M, 0.08 mmol) was added under stirring at room temperature, and then heated and stirred at 120°C under reflux for 6 h. After the reaction was completed, Saturated sodium bicarbonate solution was added to the reaction flask to quench the reaction, extracted with ethyl acetate, the organic phase was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate by silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain yellow solid indole[1,2-c]quinazoline 2b (67 mg, 54%). The characterization data for this compound are as follows: 1 H NMR (CDCl 3 ,600MHz)δ2.51(s,3H),6.56(d,J=8.4Hz,1H),6.98(t,J=8.4Hz,1H),7.23(s,1H),7.28(t,J=7.2 Hz, 1H), 7.39(d, J=7.2Hz, 2H), 7.46(t, J=7.8Hz, 1H), 7.51(t, ...

Embodiment 3

[0018]

[0019] According to the method described in Example 1, N-(2-(1H-indol-2-yl)phenyl)benzamide 1c (136.8 mg, 0.4 mmol), 1,4 -Dioxane (2 mL) and CuBr (5.7 mg, 0.04 mmol), dilute hydrochloric acid (0.16 mL, 0.5 M, 0.08 mmol) was added under stirring at room temperature, and then heated and stirred at 120°C under reflux for 6 h. After the reaction was completed, Saturated sodium bicarbonate solution was added to the reaction flask to quench the reaction, extracted with ethyl acetate, the organic phase was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate by silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain indole[1,2-c]quinazoline 2c (74 mg, 57%) as a yellow solid. The characterization data for this compound are as follows: 1 H NMR (CDCl 3 ,600MHz)δ3.93(s,3H),6.63(d,J=9.0Hz,1H),7.01(t,J=7.2Hz,1H),7.11(d,J=8.4Hz,2H),7.25( s, 1H), 7.30(t, J=7.2Hz, 1H), 7.48(t, J=7.8Hz, 1H), 7.5...

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Abstract

The invention discloses a method for synthesizing indole[1,2-c]quinazoline compounds, and belongs to the technical field of organic synthesis. The technical scheme of the invention is that the methodfor synthesizing the indole[1,2-c]quinazoline compounds comprises the following steps: placing an N-(2-(1H-indol-2-yl)phenyl)benzamide compound, 1,4-dioxane and cuprous bromide into a reaction vessel,adding dilute hydrochloric acid under stirring at room temperature, and carrying out a reflux reaction at 120 DEG C until the reaction is completed through the monitoring by using thin-layer chromatography(TLC), so that an indole[1,2-c]quinazoline compound is finally obtained. The method provided by the invention has the advantages of mild reaction condition, simple operation and wide substrate application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing indole[1,2-c]quinazoline compounds. Background technique [0002] Indoloquinazolines have been widely studied by organic chemists in recent years because of their widespread presence in natural products and synthetic drugs with important physiological activities. Among them, the compounds containing indole[1,2-c]quinazoline structure often show strong activity in the field of antibacterial and antifungal. Although the synthesis methods of indole[1,2-c]quinazoline compounds have been reported in the literature, these literature methods still have many shortcomings such as unsuitable preparation of raw materials, cumbersome operation steps and low yields, which to a large extent This restricts the scope of application of this type of synthesis method. Therefore, it is necessary to develop a mild and efficient new method for the synthesis of the...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 郭胜海刘扬凡王芳陶丽范学森
Owner HENAN NORMAL UNIV
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