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Pyrrole[3, 2-c]quinoline compound and preparation method thereof

A 2-c compound technology, which is applied in the field of pyrrolo[3,2-c]quinoline compounds and their preparation, can solve the problems of difficult synthesis of raw materials and difficult diversity synthesis, and achieve wide substrate applicability, The effect of the low cost of the catalytic system and the simplicity of the method

Active Publication Date: 2020-06-02
JIAXING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method requires pre-synthesis of pyrrole compounds, and the synthesis of raw materials is difficult
Moreover, it is difficult to achieve diverse synthesis by using this reaction

Method used

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  • Pyrrole[3, 2-c]quinoline compound and preparation method thereof
  • Pyrrole[3, 2-c]quinoline compound and preparation method thereof
  • Pyrrole[3, 2-c]quinoline compound and preparation method thereof

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preparation example Construction

[0026] The invention provides a kind of preparation method of pyrrolo[3,2-c]quinoline compound, comprising the following steps:

[0027] mixing N-propargyl-iodoaniline derivatives, tert-butyl isocyanide, a palladium catalyst, a base and an organic solvent, and performing an isocyanine insertion reaction to obtain a pyrrolo[3,2-c]quinoline compound;

[0028] The N-propargyl-iodoaniline derivatives have a structure shown in formula I:

[0029]

[0030] Among them, R 1 including sulfonyl or carbonyl; R 2 Including hydrogen, alkyl, aryl or heterocyclic aryl; R 3 Including hydrogen, bromine or heteroaryl, X is C or N.

[0031] In the present invention, unless otherwise specified, the required preparation materials are commercially available products well known to those skilled in the art.

[0032] In the present invention, the N-propargyl-iodoaniline derivatives have the structure shown in formula I:

[0033]

[0034] Among them, R 1 including sulfonyl or carbonyl; R 2...

Embodiment 1

[0048]

[0049] Compound 1a (0.2mmol), tert-butylisonitrile (0.8mmol), cesium carbonate (0.3mmol) and tetrakis-(triphenylphosphine)palladium (0.01mmol) in the above equation were added to 2mL of toluene, under nitrogen atmosphere , the reaction solution was heated to 110° C., the isocyanine intercalation reaction was carried out for 8 hours, the obtained reaction solution was filtered, and then the obtained filtrate was subjected to column chromatography to obtain the target product 3a, and the separation yield was 61%.

[0050] The compound prepared in embodiment 1 is carried out NMR characterization, and the results are as follows:

[0051] 1 H NMR (400MHz, cdcl 3 )δ7.75-7.71(m,1H),7.40(t,J=7.6Hz,2H),7.32-7.27(m,3H),7.17(m,J=4.7,1.8Hz,2H),7.12-7.06 (m,3H),6.98(s,1H),6.96(s,1H),4.72(s,2H),3.09(s,1H),2.26(s,3H),1.27(s,9H),0.76( s,9H).

[0052] 13 C NMR (101MHz, cdcl 3 )δ142.75,142.64,137.54,135.55,132.22,130.10,129.30,129.10,128.87,128.72,127.43,126.80,126.47,125.93,1...

Embodiment 2

[0054]

[0055] Add compound 1b (0.2 mmol), tert-butylisonitrile (1 mmol), potassium phosphate (0.4 mmol) and palladium acetate (0.01 mmol) in the above equation to 2 mL of toluene, and heat the reaction solution to 110 ° C under nitrogen atmosphere , carried out isocyanine intercalation reaction for 8h, filtered the obtained reaction solution, and then subjected the obtained filtrate to column chromatography to obtain the target product 3b, and the separation yield was: 60%.

[0056] The compound prepared in embodiment 2 is carried out NMR characterization, and the results are as follows:

[0057] 1 H NMR (400MHz, cdcl 3 )δ=7.95(m,1H),7.86(d,J=8.2,1H),7.61(d,J=8.5,2H),7.53(s,4H),7.28(d,J=8.0,2H), 7.22(m,2H),7.02(d,J=7.9,2H),4.70(s,1H),4.42(d,J=17.2,1H),2.33(s,3H),1.35(s,9H), 0.62(s,9H).

[0058] 13 C NMR (101MHz, cdcl 3 )δ144.74,142.93,137.43,134.04,132.61,132.59,131.79,131.11,130.49,129.41,128.99,128.46,128.10,127.71,127.40,127.15,126.84,126.38,125.82,125.56,125.19,...

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Abstract

The invention provides a pyrrole[3, 2-c]quinoline compound and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method of the pyrrole[3, 2-c]quinoline compound provided by the invention comprises the following steps of: mixing an N-propargyl-iodoaniline derivative, tert-butyl isocyanide, a palladium catalyst, alkali and an organic solvent, andcarrying out isocyan insertion reaction to obtain the pyrrole[3, 2-c]quinoline compound. According to the method, under the action of the palladium catalyst, a series of simple and easily available N-propargyl-iodoaniline derivatives are used as the raw materials, synthesis of a series of pyrrole[3, 2-c]quinoline compounds is realized by utilizing an isocyan secondary insertion reaction, and the method is simple, rapid, the catalytic system is low in cost, and the substrate applicability is wide.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a pyrrolo[3,2-c]quinoline compound and a preparation method thereof. Background technique [0002] Pyrrolo[3,2-c]quinoline compounds are an important class of heterocyclic compounds existing in nature, and many drugs or drug intermediates contain pyrrolo[3,2-c]quinoline structural units. More and more studies have shown that isoquinolinone derivatives have pharmacological activities such as anti-inflammatory, analgesic, anti-tumor and anti-bacterial fungi. For example: isocryptolepine, a natural product with a pyrrole [3,2-c] quinoline skeleton, has good antimalarial properties (Agarwal, P.K.; et al. New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet– Spengler Reaction, Eur. J. Org. Chem. 2009, 292). Therefore, it is particularly important to develop simple and efficient methods for synthesizing isoquinolinone ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D471/14
CPCC07D471/04C07D471/14
Inventor 邱观音生黄棵棵刘晋飙
Owner JIAXING UNIV
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