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Substituted aza [5] helicene derivative as well as preparation method and application thereof

A derivative and helicene technology, which is applied in the field of substituted aza[5]helicene derivatives and their preparation, can solve the problems of large limitations, violations, and difficult modification of substrates, and achieves a simple and easy-to-operate preparation method. Fluorescence intensity, step-economy effect

Pending Publication Date: 2022-07-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the preparation of such helicene compounds usually requires the use of complex substrates and metal reagents, which can only be obtained through multi-step synthesis, and the substrates are limited and difficult to modify, which violates the current concept of "high efficiency and green".

Method used

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  • Substituted aza [5] helicene derivative as well as preparation method and application thereof
  • Substituted aza [5] helicene derivative as well as preparation method and application thereof
  • Substituted aza [5] helicene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Synthesis of Compound 21

[0050] Under argon protection, 0.1 mmol of benzoquinoline (compound corresponding to No. (1), 0.0179 g), 0.3 mmol of diphenyliodonium salt (compound corresponding to No. (18), 0.1184 g), 0.005 mmol of Pd 2 (dba) 3 (0.0046g), 0.2mmol sodium carbonate (0.0212g) was added to an 8mL reaction flask, then 2mL of o-dichlorobenzene was added as a reaction solvent, and the reaction was stirred at 140°C for 24h. After the reaction, the reaction solution is separated by vacuum evaporation and column chromatography (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase changes. The volume ratio of ethyl acetate and petroleum ether is 1:60~1:40) to obtain 0.0230g of reaction product.

[0051] The above reaction products were characterized, and the results were:

[0052] 1 H NMR (400MHz, CDCl 3 )δ8.69-8.55(m,5H),...

Embodiment 2

[0054] Example 2: Synthesis of Compound 22

[0055] Under argon protection, 0.1 mmol of 2-methylbenzo[h]quinoline (compound corresponding to No. (2), 0.0193 g), 0.3 mmol of diphenyliodonium salt (compound corresponding to No. (18), 0.1184 g), 0.005 mmol Pd 2 (dba) 3 (0.0046g), 0.2mmol sodium carbonate (0.0212g) was added to an 8mL reaction flask, then 2mL of o-dichlorobenzene was added as a reaction solvent, and the reaction was stirred at 140°C for 24h. After the reaction, the reaction solution is separated by vacuum evaporation and column chromatography (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase changes. The volume ratio of ethyl acetate and petroleum ether is 1:60~1:40) to obtain 0.0210g of reaction product.

[0056] The above reaction products were characterized, and the results were:

[0057] 1 H NMR (400MHz, CDCl 3 )δ8.71-8....

Embodiment 3

[0059] Example 3: Synthesis of Compound 23

[0060] Under argon protection, 0.1 mmol of 3-methylbenzo[h]quinoline (compound corresponding to No. (3), 0.0193 g), 0.3 mmol of diphenyliodonium salt (compound corresponding to No. (18), 0.1184 g), 0.005 mmol Pd 2 (dba) 3 (0.0046g), 0.2mmol sodium carbonate (0.0212g) was added to an 8mL reaction flask, 2mL of o-dichlorobenzene was added as a reaction solvent, and the reaction was stirred at 140°C for 24h. After the reaction, the reaction solution is separated by vacuum evaporation and column chromatography (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase changes. The volume ratio of ethyl acetate and petroleum ether is 1:60~1:40) to obtain 0.0210g of reaction product.

[0061] The above reaction products were characterized, and the results were:

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.70-8.62(m,...

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Abstract

The invention discloses a substituted aza [5] helicene derivative and a preparation method and application thereof, the aza [5] helicene derivative has the following structural general formula: wherein the substitution site of R1 is any one of 1-7, the substitution site of R2 is any one of 8-11, and the substitution site of R3 is any one of 12-15; r1 is selected from one of hydrogen, C1-C5 alkyl, halogen, phenyl, substituted phenyl, naphthyl, thienyl, dibenzothienyl, furyl and N-phenyl carbazolyl, and R2 and R3 are respectively and independently selected from one of hydrogen and C1-C5 alkyl. The aza [5] helicene derivative is obtained by reacting benzo [h] quinoline and a diaryl cyclic high-iodine reagent in the presence of a metal palladium catalyst and alkali, the preparation method is simple and efficient, raw materials are easy to obtain, a substrate is easy to modify, and the aza [5] helicene derivative conforms to the green chemistry concept; in addition, the prepared aza [5] helicene derivative has potential application value in the fields of photoelectric materials, organic small molecule catalysis and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a substituted aza[5]helicene derivative and a preparation method and application thereof. Background technique [0002] Helicene compounds are a class of ortho-fused polycyclic aromatic compounds with non-planar structures. In the past few decades, helicenes have been widely used in the development of nonlinear optical materials, chiral optical materials, organic small molecule catalysis and even anticancer drugs. For example, chiral aza[6] helicenes can be used as organic small molecule catalysts for the synthesis of complex chiral alcohols, and can also be used for the development of nonlinear optoelectronic materials; while helicene salts can be used to damage DNA. Inhibitory effect of kidney cancer, lung cancer, leukemia and other cancer cells. [0003] [0004] At present, the preparation of such helicene compounds usually requires the use of complex substrate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D403/10C07D405/04C07D409/04C09K11/06
CPCC07D221/18C07D409/04C07D405/04C07D403/10C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092Y02E10/549
Inventor 纪顺俊蔡忠建徐一鑫
Owner SUZHOU UNIV
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