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Multi-substituted indene amine derivative and preparation method thereof

A derivative and multi-substitution technology, which is applied in the field of multi-substituted indenamine derivatives and their preparation, can solve the problems of unfavorable expansion of the substrate range, and achieve the effects of simple post-treatment, wide substrate range and high yield

Active Publication Date: 2019-03-08
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these strategies all focus on the intermolecular cyclization between aromatic imines and alkynes, which is very unfavorable for expanding the scope of substrates.

Method used

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  • Multi-substituted indene amine derivative and preparation method thereof
  • Multi-substituted indene amine derivative and preparation method thereof
  • Multi-substituted indene amine derivative and preparation method thereof

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Experimental program
Comparison scheme
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Embodiment 1

[0022] Preparation of product 1

[0023]

[0024] 0.2 mmol of ethyl benzimidate, 0.4 mmol of 1,3-diphenyl-2-propen-1-one, [Cp*Rh(MeCN) 3 ](SbF 6 ) 2 Add 0.01mmol, 0.2mmol of 1-adamantanecarboxylic acid, and 2mL of 1,2-dichloroethane into a 5mL reaction flask, and react at 120°C for 36h. After cooling to room temperature, 0.2 mmol of sodium carbonate was added and stirred for 1 h. After distilling off 1,2-dichloroethane, 54.7 mg of the target product 1 was obtained after purification by column chromatography with a yield of 88%. The characterization data of this compound are as follows: 1 H NMR (400MHz, DMSO) δ8.71(s, 2H), 8.07-8.01(m, 1H), 7.44-7.34(m, 4H), 7.28-7.17(m, 3H), 7.17-7.07(m, 1H ), 6.99-6.89(m, 3H), 6.81-6.73(m, 2H), 5.28(s, 1H). 13 C NMR (100MHz, DMSO) δ191.3, 161.9, 150.6, 142.8, 142.3, 136.6, 130.8, 129.4, 128.3, 128.0, 127.6, 127.4, 127.2, 126.2, 125.1, 122.0, 110.8, 52.7. Calc MS (ESI) for C 22 h 17 NO[M+H] + 312.1383; found 312.1386.

Embodiment 2

[0026] 0.2 mmol of ethyl benzimidate, 0.4 mmol of 1,3-diphenyl-2-propen-1-one, [Cp*RhCl 2 ] 2 0.005mmol, AgSbF 6 Add 0.02mmol, 0.2mmol of 1-adamantanecarboxylic acid, and 2mL of 1,2-dichloroethane into a 5mL reaction flask, and react at 120°C for 36h. After cooling to room temperature, 0.2 mmol of sodium carbonate was added and stirred for 1 h. After 1,2-dichloroethane was distilled off, 43.5 mg of the target product 1 was obtained after purification by column chromatography with a yield of 70%.

Embodiment 3

[0028] 0.2 mmol of ethyl benzimidate, 0.4 mmol of 1,3-diphenyl-2-propen-1-one, [Cp*RhCl 2 ] 2 0.005mmol, AgNTf 2 Add 0.02mmol, 0.2mmol of 1-adamantanecarboxylic acid, and 2mL of 1,2-dichloroethane into a 5mL reaction flask, and react at 120°C for 36h. After cooling to room temperature, 0.2 mmol of sodium carbonate was added and stirred for 1 h. After distilling off 1,2-dichloroethane, 47.3 mg of the target product 1 was obtained after purification by column chromatography, with a yield of 76%.

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Abstract

The invention discloses a multi-substituted indene amine derivative and a preparation method thereof. The structural formula is shown in the description, wherein R1 is halogen, alkyl, aryl or alkoxy,R2 is aryl or alkyl, and R3 is acyl or nitryl. The indene amine derivative with multiple substituent groups is synthesized and has profound significance in the aspect of medicinal chemistry. The raw materials used in the preparation method are easy to obtain, and the preparation method is high in yield, good in area selectivity, wide in substrate range and convenient in after-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a polysubstituted indenamine derivative and a preparation method thereof. Background technique [0002] Indenamine is a key backbone in many bioactive molecules, such as indatraline, tefludazine, cis-[ 13 C] DDPI. Therefore, the research on new synthesis methods of multi-substituted indenamine compounds and their analogues has important application value and has attracted the attention of researchers in related fields. [0003] In recent years, transition metal-catalyzed C-H bond activation / intermolecular cyclization reactions to synthesize indenamines have attracted the attention of organic synthetic chemists. However, these strategies all focus on the intermolecular cyclization between aromatic imines and alkynes, which is very unfavorable for expanding the scope of substrates. Based on the structural diversity of indenamines and their wide application ...

Claims

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Application Information

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IPC IPC(8): C07C225/20C07C221/00C07C211/42C07C209/00
CPCC07C209/00C07C211/42C07C221/00C07C225/20C07C2602/08
Inventor 崔秀灵伍斌杰
Owner HUAQIAO UNIVERSITY