Method for preparing benzothiazole quinazoline derivatives through catalysis

A technology for preparing benzothiazoquinazoline and catalysis, which is applied in the fields of chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., and can solve the problems of less recyclable times, large amount of catalyst usage, and complicated operation process and other problems, to achieve the effect of more recycling times, shorter reaction time and high catalytic activity

Active Publication Date: 2017-07-21
东营睿港投资服务有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the shortcomings of the existing benzothiazoquinazoline derivatives preparation process, which usually has the disadvantage...

Method used

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  • Method for preparing benzothiazole quinazoline derivatives through catalysis
  • Method for preparing benzothiazole quinazoline derivatives through catalysis
  • Method for preparing benzothiazole quinazoline derivatives through catalysis

Examples

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preparation example Construction

[0034] For the preparation method of the bissulfonate acidic ionic liquid catalyst, see the relevant literature (Novel multiple-acidic ionic liquids: catalysts for environmentally friendly benign synthesis of trans-β-nitrostyrenes under solvent-free conditions, Industrial & Engineering Chemistry Research, 2014, 53: 547~ 552).

[0035] A kind of method for catalyzing the preparation of benzothiazole quinazoline derivatives provided by the present invention, the specific technical process is shown in figure 1 , the chemical reaction formula of this reaction is:

[0036]

[0037] Wherein the molar ratio of 2-aminobenzothiazole derivative (1), α-tetralone (2) and aldehyde (3) in the reaction is 1:1:(1~1.1), and the bissulfonate acidic ionic liquid catalyst The molar dosage is 5~8% of the molar amount of the 2-aminobenzothiazole derivative used, and the volume of the reaction solvent water in millimoles is 5~8% of the molar amount of the 2-aminobenzothiazole derivative in milli...

Embodiment 1

[0044] Add 1mmol of 4-chloro-2-aminobenzothiazole, 1mmol of α-tetralone, 1mmol of furfuraldehyde and 0.06mmol of bissulfonate acidic ionic liquid to 25ml of single port with stirring bar and condenser tube filled with 5ml of water in the bottle. Reaction at 68°C for 29min, followed by TLC (thin plate chromatography), cooled to room temperature after the reaction, crushed the precipitated solid, let stand, filtered with suction, washed the filter residue with ethanol (3ml×3), and dried in vacuo to obtain 9- Chloro-7-(furan-2-yl)-5,6-dihydro-7H-benzo[h]benzothiazo[2,3-b]quinazoline, the yield is 88%, make up 5ml with water The final filtrate was directly added with 4-chloro-2-aminobenzothiazole, α-tetralone and furanformaldehyde and reused, and the collected ethanol washing liquid was used for the next washing.

[0045] The performance parameters of 9-chloro-7-(furan-2-yl)-5,6-dihydro-7H-benzo[h]benzothiazo[2,3-b]quinazoline obtained in this example are: m.p.219~221℃; IR(KBr):...

Embodiment 2～5

[0051] The preparation methods of Examples 2-5 are basically the same as in Example 1, the difference mainly lies in the different reaction temperatures. The specific reaction temperatures and the yields of the products obtained in each embodiment are shown in Table 2.

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Abstract

The invention discloses a method for preparing benzothiazole quinazoline derivatives through catalysis and belongs to the technical field of ionic liquid catalysis. In the preparation reaction, the molar ratio of 2-aminobenzothiazole derivative to alpha-tetralone to aldehyde is 1:1:(1-1.1), the molar use amount of a double sulfonate radical acidic ionic liquid catalyst is 5 to 8 percent of the molar use amount of 2-aminobenzothiazole derivative, the volume amount of reaction solvent water based on milliliter is 5 to 7 times of the molar weight of the 2-aminobenzothiazole derivative based on millimole, the reaction temperature is 65 to 78 DEG C, and the reaction time is 24 to 57 minutes; after the reaction, cooling is conducted to room temperature, suction filtration is conducted, and the filter residue is washed with ethanol and vacuum-dried to obtain the benzothiazole quinazoline derivatives. Compared with the existing preparation method, the method for preparing the benzothiazole quinazoline derivatives through catalysis has the characteristics that the use amount of catalyst is small, the catalytic activity is stable, biodegradation is facilitated, the whole preparation process is simple and convenient to operate, and the greening degree is high; and industrialized large-scale production is realized easily.

Description

technical field [0001] The invention belongs to the technical field of ionic liquid catalysis, in particular to a method for catalyzing the preparation of benzothiazolequinazoline derivatives. Background technique [0002] Among nitrogen-containing heterocyclic compounds, quinazoline derivatives are very important structural units, and they exist in a variety of natural biologically active substances, such as prazosin, lapatinib, icoti Ni et al. Quinazoline derivatives have many biological and pharmaceutical activities, making them widely used in pesticides, medicine and other fields, such as sterilization, insecticide, anti-cancer, anti-virus and so on. In addition, compounds with benzothiazole structures are also an important class of functional compounds, which have important application prospects in nonlinear optics, electroluminescence and photochromic materials. Therefore, it is very important to study the preparation of benzothiazole-quinazoline derivatives containi...

Claims

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Application Information

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IPC IPC(8): C07D513/04B01J31/02
CPCB01J31/0285C07D513/04
Inventor 沈建忠卢华
Owner 东营睿港投资服务有限责任公司
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