The synthetic method of 2-cyclopropyl-8-methylquinazoline

A technology of methylquinazoline and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of environmental friendliness and atom economy, and achieve the effects of shortening reaction time, high reaction efficiency and easy operation

Active Publication Date: 2020-05-05
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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  • The synthetic method of 2-cyclopropyl-8-methylquinazoline
  • The synthetic method of 2-cyclopropyl-8-methylquinazoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 15ml high-pressure tube, add 51.41mg (0.375mmol) (2-amino-3-methylphenyl) methanol, 16.76mg (0.25mmol) cyclopropylcarbonitrile, 5.1mg (0.3equiv) sodium ethoxide, 1mL tert Amyl alcohol was stirred magnetically under an air atmosphere, and reacted at 130° C. for 2 h. After TLC analysis, No Reaction.

Embodiment 2

[0021] The synthetic method of the 2-cyclopropyl-8-methylquinazoline of the present embodiment, the steps are as follows:

[0022] In a 15ml high-pressure tube, add 51.41mg (0.375mmol) (2-amino-3-methylphenyl) methanol, 16.76mg (0.25mmol) cyclopropylcarbonitrile, 1.93mg (1mol%) pincer metal ruthenium ( II) Compound, 5.1 mg (0.3 equiv) sodium ethoxide, 1 mL tert-amyl alcohol, magnetically stirred under air atmosphere, reacted at 130° C. for 2 h. According to TLC analysis, the raw material cyclopropylcarbonitrile had reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the quality of the product 2-cyclopropyl-8-methylquinazoline was 20.6 mg, and the yield was 45%. product by 1 H NMR, 13 Confirmed by C NMR. 1 H NMR (600MHz, CDCl3) δ9.18 (s, 1H), 7.65 (d, J = 7.5Hz, 2H), 7.39 (t, J = 7.5Hz, 1H), 2.71 (s, 3H), 2.47–2.38 (m,1H),1.30–1.23(m,2H),1.15–1.09(m,2H).13C NMR(101MHz,CDCl3)δ167.4,160.2,149.5,135.9,133.6,125.8,124.8,123....

Embodiment 3

[0024] The synthetic method of the 2-cyclopropyl-8-methylquinazoline of the present embodiment, the steps are as follows:

[0025] In a 15ml high-pressure tube, 34.27mg (0.25mmol) (2-amino-3-methylphenyl) methanol, 16.76mg (0.25mmol) cyclopropylcarbonitrile, 1.93mg (1mol%) pincer metal ruthenium (II ) compound, 6.0 mg (0.6 equiv) of sodium hydroxide, 1 mL of 1,4-dioxane, magnetically stirred in an air atmosphere, and reacted at 130° C. for 2 h. According to TLC analysis, the raw material cyclopropylcarbonitrile had reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 2-cyclopropyl-8-methylquinazoline was 30.2 mg, and the yield was 66%.

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Abstract

The invention discloses a method for synthesizing 2-cyclopropyl-8-methylquinazoline. The method comprises: orderly adding (2-amino-3-methylphenyl)methanol, cyclopropyl formonitrile, a catalyst, a baseand 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 and the 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 2-cyclopropyl-8-methylquinazoline. 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.Drugs Future,2009,34,618.Eur.J.Med.Chem.,2014,80,447.J.Mol.Struct.,2017,1130,895.) Oxazolines play an important role in therapy and pharmacological applications. In recent years, the research on the construction of quinazolines has become increasingly mature. [0003] Most of the reported methods for constructing quinazolines require equal amounts of oxidizing agents, prefunctionali...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06
CPCC07D215/06
Inventor 赵雪梅刘子琳碗晓敏王亚改王秋灵朱新举郝新奇宋毛平
Owner ZHENGZHOU UNIV
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