Method for synthesizing 6-chloro-2-(thienyl-2-yl)quinazoline

A synthetic method, thienyl technology, applied in the direction of organic chemistry, can solve the problems of environmental friendliness and atom economy, and achieve the effect of shortening the reaction time, high reaction efficiency and easy operation

Inactive Publication Date: 2019-01-11
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the reported methods for constructing quinazolines require equal amounts of oxidizing agents, prefunctionalized substrates, or external additives, which are not environmentally friendly and atom-economical.

Method used

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  • Method for synthesizing 6-chloro-2-(thienyl-2-yl)quinazoline
  • Method for synthesizing 6-chloro-2-(thienyl-2-yl)quinazoline
  • Method for synthesizing 6-chloro-2-(thienyl-2-yl)quinazoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 15ml high-pressure tube, add 58.89mg (0.375mmol) (2-amino-5-chlorophenyl) methanol, 27.25mg (0.25mmol) 2-cyanothiophene, 5.1mg (0.3equiv) sodium ethoxide, 2mL toluene, Stir magnetically under an air atmosphere, and react for 4 hours at a temperature of 130°C. After TLC analysis, No Reaction.

Embodiment 2

[0021] The synthetic method of the 6-chloro-2-(thienyl-2-yl) quinazoline of the present embodiment, the steps are as follows:

[0022] In a 15ml high-pressure tube, add 58.89mg (0.375mmol) (2-amino-5-chlorophenyl) methanol, 27.25mg (0.25mmol) 2-cyanothiophene, 1.93mg (1mol%) pincer metal ruthenium (II ) compound, 5.1mg (0.3equiv) sodium ethoxide, 2mL tert-butanol, magnetically stirred under air atmosphere, and reacted at 130°C for 4h. According to TLC analysis, the raw material 2-cyanothiophene had reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 6-chloro-2-(thienyl-2-yl)quinazoline has a mass of 22.5 mg and a yield of 35%. product by 1 H NMR, 13 Confirmed by C NMR. 1 H NMR (400MHz, CDCl3) δ9.28(d, J=0.5Hz, 1H), 8.14(dd, J=3.7, 1.2Hz, 1H), 7.95(d, J=9.0Hz, 1H), 7.85(d ,J=2.3Hz,1H),7.80(dd,J=9.0,2.3Hz,1H),7.53(dd,J=5.0,1.2Hz,1H),7.21-7.16(m,1H).13C NMR(101MHz , CDCl3) δ159.6, 158.1, 149.1, 143.4, 135.3, 1...

Embodiment 3

[0024] The synthetic method of the 6-chloro-2-(thienyl-2-yl) quinazoline of the present embodiment, the steps are as follows:

[0025] In a 15ml high-pressure tube, 39.26mg (0.25mmol) (2-amino-5-chlorophenyl) methanol, 27.25mg (0.25mmol) 2-cyanothiophene, 1.93mg (1mol%) pincer metal ruthenium (II) Compound, 16.83 mg (0.6 equiv) of potassium tert-butoxide, 2 mL of a mixed solution of acetonitrile and tert-butanol, magnetically stirred under an air atmosphere, and reacted at 130° C. for 4 hours. According to TLC analysis, the raw material 2-cyanothiophene had reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 6-chloro-2-(thienyl-2-yl)quinazoline was 40.3 mg, and the yield was 67%.

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Abstract

The invention discloses a method for synthesizing 6-chloro-2-(thienyl-2-yl)quinazoline. The method comprises: orderly adding (2-amino-5-chlorophenyl)methanol, 2-thiophenecarbonitrile, a catalyst, a base and a solvent into a reactor and carrying out magnetic stirring in air for a full reaction in an oil bath pot. The method utilizes alcohol as a starting material for the formation of C-N bonds andthe alcohol is cheap, easy to treat and environmentally friendly. The method solves the problem that the conventional method utilizes various oxidizing agents to produce a large amount of by-products.The method utilizes an NNN type pincerlike metal ruthenium (II) compound as a catalyst for the catalytic reaction so that the reaction is finished in one step, the reaction time is greatly shortened,operation is simple and the reaction efficiency is high. The method satisfies the green chemistry sustainable development requirements.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 6-chloro-2-(thienyl-2-yl)quinazoline. Background technique [0002] Quinazolines are a very important and common class of nitrogen heterocyclic compounds, and their derivatives often exist in various alkaloids and functional molecules, and have a variety of biological and pharmacological activities: such as anticancer, antimalarial, anti-inflammatory, antibacterial , anticonvulsant, antituberculous and antihypertensive properties. (Med.Chem.Res., 2013,23,1397.DrugsFuture,2009,34,618.Eur.J.Med.Chem.,2014,80,447.J.Mol.Struct.,2017,1130,895.) Quinazoline plays an important role in therapy and pharmacological applications. In recent years, the research on the construction of quinazoline has become increasingly mature. [0003] Most of the reported methods for constructing quinazolines require equal amounts of oxidizing agents, prefunction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04
CPCC07D409/04
Inventor 郝新奇颜花婷田露露碗晓敏朱钰深朱新举刘国际宋毛平
Owner ZHENGZHOU UNIV
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