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Azepine fused ring derivatives as well as preparation method and application thereof

A technology for azapine and derivatives, applied in the field of azapine fused ring derivatives and their preparation, can solve the problems that the types cannot meet people’s needs, achieve rich diversity and product types, simple and fast preparation, and rapid build effect

Active Publication Date: 2019-06-07
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the types they exist in nature cannot meet people's needs, and need to be broadened.

Method used

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  • Azepine fused ring derivatives as well as preparation method and application thereof
  • Azepine fused ring derivatives as well as preparation method and application thereof
  • Azepine fused ring derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] In this example, 3,6-dimethyl-6H-indeno[1,7-bc]aza-5-carbaldehyde (1a) was prepared, and its reaction formula is as follows:

[0067]

[0068] Under an atmosphere of atmospheric pressure air, add ethyl benzimidate compound 2a (30.0mg, 0.20mmol), crotonaldehyde 3a (24μL, 0.40mmol), trivalent rhodium catalyst [Cp*Rh (CH 3 EN) 3 ][SbF 6 ] 2 (0.002mmol), sodium acetate (5.0mg, 0.06mmol) and 1,2-dichloroethane (DCE, 1mL), at a temperature of 100 ° C for 3h for the first reaction, TLC detection of benziminoic acid ethyl After the ester compound 2a was reacted, butenone 4a (24 μL, 0.40 mmol) was added to carry out the second reaction for 9 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain the crude product. The crude product was chromatographically separated on a prepared silica gel plate, and the selected developer or eluent was petroleum ether and ethyl acetate at a volume ratio ...

Embodiment 2

[0072] In this example, the preparation of 6-methyl-3-phenyl-6H-indeno[1,7-bc]aza-5-carbaldehyde (1b) is carried out, and its reaction formula is as follows:

[0073]

[0074] Under an atmospheric pressure air atmosphere, add ethyl benzimidate compound 2a (30.0mg, 0.20mmol), crotonaldehyde 3a (30μL, 0.50mmol), trivalent rhodium catalyst [Cp*RhCl 2 ] 2 (0.002mmol), silver trifluoromethanesulfonimide (0.006mmol), copper acetate (4mg, 0.02mmol), sodium acetate (1.60mg, 0.02mmol) and 1,2-dichloroethane (DCE, 1mL) , the first reaction was carried out at a temperature of 100°C for 3h, and after the reaction of ethyl benzimidate compound 2a was detected by TLC, butenone 4a (30μL, 0.50mmol) was added, and the second reaction was carried out for 9h. After completion, cool to room temperature, filter through diatomaceous earth, and concentrate to obtain a crude product. The crude product was separated by chromatography on the prepared silica gel plate, and the selected developer or...

Embodiment 3

[0077] In this example, the preparation of 1-(6-methyl-3-phenyl-6H-indeno[1,7-bc]azepine-5-yl)-ethanone (1c) is carried out, and its reaction formula is as follows :

[0078]

[0079] Under an atmosphere of atmospheric pressure air, add ethyl benzimidate compound 2a (30.0mg, 0.20mmol), 3-penten-2-one 3b (30μL, 0.50mmol), trivalent Rhodium catalyst [Cp*RhCl 2 ] 2 (0.004mmol), silver trifluoromethanesulfonimide (0.01mmol), copper acetate (4mg, 0.02mmol), sodium acetate (1.6mg, 0.02mmol) and 1,2-dichloroethane (DCE, 1mL) , the first reaction was carried out at a temperature of 100° C. for 3 h. After the reaction of ethyl benzimidate compound 2a was detected by TLC, phenyl enone 4b (30 μL, 0.50 mmol) was added, and the second reaction was carried out for 9 h. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared sili...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to azepine fused ring derivatives as well as a preparation method and application thereof. The azepine fused ring derivatives provided by the invention have a structural formula represented by a formula (I) shown in the description, wherein Ar is an aryl group selected from an aromatic heterocyclic group,a phenyl group and an aromatic fused ring group; R<1> is one selected from hydrogen, a halogen element or a functional group-containing hydrocarbon group; R<2> is an alkyl group; and R<3> and R<4> areselected from hydrogen, an alkyl group or an aryl group. According to the azepine fused ring derivatives represented by the formula (I) provided by the invention, each azepine fused ring derivative contains a five-membered ring, a six-membered ring and a seven-membered ring at the same time, and contains an easily-converted aldehyde functional group or a carbonyl functional outside the ring, thereby facilitating subsequent conversion and having good application prospects in the fields of biology, drugs and natural products.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an azepine condensed ring derivative and its preparation method and application. Background technique [0002] Azapine fused ring derivatives are widely used in human production and life. Azapine is a very important class of nitrogen-containing heterocyclic skeletons. It is not only an important skeleton in organic synthesis, but also exists in many natural products and has Physiologically active compounds, such as common drugs such as Fawcettimine, Akagerine, Galantamine, Cephalotaxine and Stemoamide, and Natural products all contain the skeleton of azepine and its derivatives. Azapine fused ring derivatives have strong physiological activity and medicinal value, and are also used as the core skeleton of best-selling drugs for treating mental diseases. However, the types they exist in nature cannot meet people's needs and need to be broadened. [0003] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/32A61P25/00
Inventor 李先纬饶建行霍延平
Owner GUANGDONG UNIV OF TECH
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