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4-cyano-7, 8-dihydroisoquinoline derivative as well as preparation method and application thereof

A technology of dihydroisoquinoline and derivatives, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of expensive use, complicated steps, toxic metal catalysts, etc.

Active Publication Date: 2021-05-04
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Quinoline and isoquinoline units are traditional and important scaffolds for constructing various fluorescent materials, but unlike quinoline, isoquinoline is usually used to construct fluorescent molecules of metal complexes, and is rarely found in pure organic fluorescent compounds. to report
[0003] In addition, although some effective synthetic methods for constructing isoquinoline structures have been reported, these methods often have disadvantages such as cumbersome steps, harsh reaction conditions, and the use of expensive or toxic metal catalysts.
In addition, there are few reports on isoquinoline-related structures, and it is of great significance to provide new isoquinoline-related structures

Method used

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  • 4-cyano-7, 8-dihydroisoquinoline derivative as well as preparation method and application thereof
  • 4-cyano-7, 8-dihydroisoquinoline derivative as well as preparation method and application thereof
  • 4-cyano-7, 8-dihydroisoquinoline derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] This example provides 4-cyano-7,8-dihydroisoquinoline derivative 3aa and its preparation method. The synthesis route is as follows:

[0074]

[0075] Concrete synthetic steps include:

[0076] Take compound 1a 0.3mmol, secondary amine 2a 1.2mmol and sodium acetate 0.6mmol, join in 3mL of DMSO, at 120 ℃ and N 2 The reaction was stirred under atmosphere for 14 h; after the reaction was completed, after the reaction liquid was cooled to room temperature, 20 mL of CH 2 Cl 2 , with water and CH 2 Cl 2 After extraction three times, the organic phase was collected and dried with anhydrous sodium sulfate, the organic solvent was removed by rotary evaporation under reduced pressure, and the compound was purified by column chromatography to obtain the corresponding compound 3aa.

[0077] Further optimize the reaction conditions, use the above compound 1a and secondary amine 2a to prepare 3aa as a template reaction, explore the reaction conditions such as base, solvent, rea...

Embodiment 2

[0083] This example provides 4-cyano-7,8-dihydroisoquinoline derivatives 3aa-3an and their preparation methods. The synthetic route is as follows:

[0084]

[0085] The specific synthetic steps include: take compound 1a 0.3mmol, secondary amine (2a-2n) 1.2mmol and KH 2 PO 4 0.9mmol, added to 2.5mL of DMSO, at 120°C and N 2 The reaction was stirred under atmosphere for 14 h; after the reaction was completed, after the reaction liquid was cooled to room temperature, 20 mL of CH 2 Cl2 , with water and CH 2 Cl 2 After extraction three times, the organic phase was collected and dried with anhydrous sodium sulfate, the organic solvent was removed by rotary evaporation under reduced pressure, and the compound was purified by column chromatography to obtain the corresponding compound 3aa-3an.

[0086] Wherein, the eluents when the compounds 3aa-3an (except 3ad and 3ag) are purified by column chromatography are as follows:

[0087] 3aa, 3ab, 3ac, 3ae, 3aj, 3al, 3an—petroleum et...

Embodiment 3

[0108] This example provides 4-cyano-7,8-dihydroisoquinoline derivative 3ba-3na and its preparation method. The synthetic route is as follows:

[0109]

[0110] The specific synthetic steps include: take compound 1b-1n 0.3mmol, secondary amine 2a 1.2mmol and KH 2 PO 4 0.9mmol, added to 2.5mL of DMSO, at 120°C and N 2 The reaction was stirred under atmosphere for 14 h; after the reaction was completed, after the reaction liquid was cooled to room temperature, 20 mL of CH 2 Cl 2 , with water and CH 2 Cl 2 After extraction three times, the organic phase was collected and dried with anhydrous sodium sulfate, the organic solvent was removed by rotary evaporation under reduced pressure, and the compound was purified by column chromatography to obtain the corresponding compound 3ba-3bn.

[0111] Wherein, the eluents when the compounds 3ba-3bn are purified by column chromatography are as follows: 3ba, 3ca, 3da, 3ea, 3fa, 3ga, 3ha, 3ia, 3ja, 3ka—petroleum ether with a volume ra...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a 4-cyano-7, 8-dihydroisoquinoline derivative as well as a preparation method and application thereof. According to the invention, symmetric and asymmetric dicyanomethylene-4H-pyran derivatives and secondary amine are used as raw materials, and a series of 4-cyano-7, 8-dihydroisoquinoline derivatives are prepared through ring opening and continuous ring closing reactions; and the reaction has the advantages of easily available raw materials, mild reaction conditions, wide substrate range, high yield and the like, is simple to operate, and avoids the defects of tedious steps, harsh reaction conditions, use of toxic and expensive metal catalysts and the like in conventional isoquinoline compound construction. The preparation method provides new possibilities for design and synthesis of isoquinoline molecules and application of the isoquinoline molecules in solid-state fluorescent materials.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 4-cyano-7,8-dihydroisoquinoline derivative and a preparation method and application thereof. Background technique [0002] Quinoline and isoquinoline units are traditional and important scaffolds for constructing various fluorescent materials, but unlike quinoline, isoquinoline is usually used to construct fluorescent molecules of metal complexes, and is rarely found in pure organic fluorescent compounds. reports. [0003] In addition, although some effective synthetic methods for constructing isoquinoline structures have been reported, these methods often have disadvantages such as cumbersome steps, harsh reaction conditions, and the use of expensive or toxic metal catalysts. In addition, there are few reports on isoquinoline-related structures, and it is of great significance to provide new isoquinoline-related structures. [0004] In view of this, the present inv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D217/22C07D409/14C09K11/06
CPCC07D401/14C07D217/22C07D409/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1007C09K2211/1092
Inventor 雷云祥张心宇黄小波吴华悦刘妙昌
Owner WENZHOU UNIVERSITY
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