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Synthesis method of benzothiazole-nitrogen-containing heterocyclic ring hybrid

The technology of a benzothiazole and a synthesis method is applied in the field of synthesis of benzothiazole-nitrogen-containing heterocyclic hybrids, and can solve the problems of low product yield and atom economy, limited preparation methods, and difficulty in obtaining raw materials, and the like, Achieve the effect of cheap raw materials, simple operation and wide application range

Active Publication Date: 2017-11-03
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although benzothiazole-nitrogen-containing heterocyclic hybrids have important application value, the methods currently available for the preparation of such compounds are very limited, and there are still problems such as unavailable raw materials, long synthetic routes, product yields and atom economy. low level problem

Method used

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  • Synthesis method of benzothiazole-nitrogen-containing heterocyclic ring hybrid
  • Synthesis method of benzothiazole-nitrogen-containing heterocyclic ring hybrid
  • Synthesis method of benzothiazole-nitrogen-containing heterocyclic ring hybrid

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Experimental program
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Effect test

Embodiment 1

[0022]

[0023] Add 1a (0.55mmol, 66μL), 2a (0.5mmol, 44μL), chlorobenzene (3mL) and iodine (0.25mmol, 63.5mg) to a 10mL Shrek tube in sequence, and place it at 120 ℃ oil bath stirring reaction for 14h. Then, 10 mL of saturated sodium thiosulfate solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with distilled water and saturated brine successively, the resulting organic phase was dried over anhydrous sodium sulfate, filtered, After spin-drying, silica gel column separation (petroleum ether / ethyl acetate=10 / 1) gave the product 3a (69.4 mg, 63%) as a white solid. The characterization data of this compound are as follows: 1 HNMR (400MHz, CDCl 3 )δ: 3.62(t, J=4.8Hz, 4H), 3.83(t, J=4.8Hz, 4H), 7.10(t, J=7.6Hz, 1H), 7.31(t, J=8.0Hz, 1H) ,7.56-7.62(m,2H). 13 C NMR (100MHz, CDCl 3 )δ: 48.5, 66.3, 119.4, 120.8, 121.7, 126.1, 130.6, 152.5, 169.0. MS: m / z 221 [M+H] + .

Embodiment 2

[0025] Add 1a (0.55mmol, 66μL), 2a (0.5mmol, 44μL), toluene (3mL) and iodine (0.25mmol, 63.5mg) to a 10mL Shrek tube in turn, and place it at 120°C after vacuumizing and filling with oxygen The reaction was stirred in an oil bath for 14h. Then, 10 mL of saturated sodium thiosulfate solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with distilled water and saturated brine successively, the resulting organic phase was dried over anhydrous sodium sulfate, filtered, After spin-drying, silica gel column separation (petroleum ether / ethyl acetate=10 / 1) gave the product 3a (38.6 mg, 35%) as a white solid.

Embodiment 3

[0027] Add 1a (0.55mmol, 66μL), 2a (0.5mmol, 44μL), dimethyl sulfoxide (3mL) and iodine element (0.25mmol, 63.5mg) to a 10mL Shrek tube in turn, vacuumize and fill it with oxygen Placed in an oil bath at 120°C and stirred for 14 hours. Then, 10 mL of saturated sodium thiosulfate solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with distilled water and saturated brine successively, the resulting organic phase was dried over anhydrous sodium sulfate, filtered, After spin-drying, silica gel column separation (petroleum ether / ethyl acetate=10 / 1) gave the product 3a (24.2 mg, 22%) as a white solid.

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Abstract

The invention discloses a synthesis method of benzothiazole-nitrogen-containing heterocyclic ring hybrid, which is obtained through series reactions between a phenyl isothiocyanate compound and a nitrogen-containing heterocyclic ring compound. The synthesis method comprises the following steps of mixing the phenyl isothiocyanate compound, the nitrogen-containing heterocyclic ring compound, a catalyst iodine and solvents, and heating to 100 to 140 DEG C for reaction under an atmosphere of oxygen or air so as to obtain the benzothiazole-nitrogen-containing heterocyclic ring hybrid. The synthesis method has the advantages the raw materials are simple and easy to obtain, the operation is simple and convenient, the condition is mild, the application range of substrates is wide and the like, and has a potential industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of a benzothiazole-nitrogen-containing heterocyclic hybrid. Background technique [0002] Benzothiazoles are an important class of heterocyclic compounds, which are widely used in medicine, pesticides, materials and other fields. The hybrid formed by benzothiazole and another nitrogen-containing heterocycle contains two types of nitrogen-containing heterocycles in the molecule. These compounds often show significant bactericidal, mildewicidal, anti-agricultural fungi, insecticidal, and herbicidal properties. , plant growth regulation and other biological and pharmaceutical activities. In addition, benzothiazole-nitrogen-containing heterocyclic hybrids are also excellent molecular building blocks and are widely used in the synthesis of various functional organic molecules. Although benzothiazole-nitrogen-containing heterocyclic hybrids ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82C07D491/113
CPCC07D277/82C07D491/113
Inventor 张新迎徐园双范学森李彬
Owner HENAN NORMAL UNIV
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