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Fused ring compound containing imidazole skeleton and preparation method thereof

A technology containing imidazole and compounds, applied in the field of condensed ring compounds containing imidazole skeleton and its preparation, can solve the problems of complex synthesis process, low synthesis efficiency, poor nucleophilicity of carbon atoms, etc., and achieve the effect of great application value

Inactive Publication Date: 2020-10-02
HUBEI UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, comprehensive literature research shows that most of the nucleophilic functional groups are concentrated on O, N and S atoms, and the use of carbon atoms as nucleophiles to capture active C(sp2)-M species is rarely reported in the literature, mainly because of The nucleophilicity of carbon atoms is relatively poor, resulting in complex synthesis processes and low synthesis efficiency

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  • Fused ring compound containing imidazole skeleton and preparation method thereof
  • Fused ring compound containing imidazole skeleton and preparation method thereof
  • Fused ring compound containing imidazole skeleton and preparation method thereof

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[0042] Further, the present invention also proposes a preparation method of a condensed ring compound containing an imidazole skeleton, using o-bromo or o-iodo aromatic aldehydes, aromatic amines and TosMIC reagents as raw materials, and obtaining imidazole under relatively mild conditions through van Leusen reaction A heterocyclic intermediate, the C-H bond at the 4th position of imidazole and the isonitrile compound are subjected to a one-step insertion reaction under the action of a palladium metal catalyst, a ligand, a base and heating to obtain a heterocyclic ring as shown in structural formula (I). In the first embodiment of the preparation method of the condensed ring compound containing imidazole skeleton provided by the invention, the preparation method comprises the following steps:

[0043] Step S10, adding the first reactant and the second reactant to anhydrous methanol and stirring and mixing, then adding TosMIC (p-toluenesulfonyl isocyanide) reagent to K 2 CO 3 ...

Embodiment 1

[0059] (1) Synthesis of Intermediate A:

[0060] ①Synthetic route:

[0061]

[0062] ②Synthesis method: Add o-bromo or o-iodobenzaldehyde (2mmol) and amine (2mmol) into a 50mL flask containing anhydrous methanol (10mL), stir at room temperature for 1h, and then add K 2 CO 3 (3mmol), TosMIC isonitrile reagent (3mmol), react 7h in the oil bath of 60 ℃; solvent, ethyl acetate and petroleum ether in a volume ratio of 1:9), intermediate A was obtained as a white solid.

[0063] Wherein, the synthesis yields of some intermediates A (intermediates A-1 to A-12) are shown in Table 1.

[0064] The synthetic yield of table 1 part intermediate A

[0065]

[0066] (2) Synthesis of the condensed ring compound containing imidazole skeleton of structure shown in structural formula (I):

[0067] ①Synthetic route:

[0068]

[0069] ②Synthesis method: In a 25mL Schlenk tube filled with toluene (5mL), add the intermediate A (1mmol), isonitrile compound (1.2mmol) and catalyst Pd(OAc...

Embodiment 2

[0076] (1) Add o-bromo or o-iodobenzaldehyde (2mmol) and amine (2mmol) into a 50mL flask containing anhydrous methanol (10mL), stir at room temperature for 1h, then add K 2 CO 3 (3mmol), TosMIC isonitrile reagent (3mmol), react 7h in the oil bath of 60 ℃; The volume ratio of solvent, ethyl acetate and petroleum ether is 1:9), and intermediate A-1 was obtained as a white solid, with a yield of 0.418g, a yield of 63%, and a melting point of 121-122°C. The compound structure test results were as follows:

[0077] 1 H NMR (CDCl 3 ,400MHz)δ(ppm)7.76(s,1H),7.55(d,J=8.0Hz,1H),7.30-7.05(m,8H); 13 C{ 1 H}NMR (CDCl 3 ,100MHz)δ(ppm)137.6,134.9,133.6,133.0,132.7,131.2,130.5,130.4,130.2,129.4,127.2,125.9,124.9; HRMS(ESI-TOF)m / z:[M+H] + Calcd for C 15 h 11 BrClN 2 332.9789; Found 332.9797.

[0078] (2) In a 25mL Schlenk tube equipped with toluene (5mL), add the intermediate A-1 (1mmol), isonitrile compound (1.2mmol) and catalyst Pd(OAc) synthesized in step (1) respectively 2 (11m...

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Abstract

The invention discloses a fused ring compound containing an imidazole skeleton and a preparation method of the fused ring compound. The fused ring compound containing the imidazole skeleton has a structure as shown in a structural formula (I) or (II). The invention provides a fused ring compound containing an imidazole skeleton. According to the method, a carbon atom is used as a nucleophilic reagent, isocyanide is inserted into the carbon atom at the fourth site of imidazole through a functionalization reaction, a new fused heterocyclic lead compound containing an indene [1, 2-d] imidazole skeleton and having potential biological activity is obtained. The method has huge potential application value in the field of synthesis of biological medicines with complex structures.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a condensed ring compound containing an imidazole skeleton and a preparation method thereof. Background technique [0002] Imidazole derivatives are multifunctional skeleton modules that exist in many important branches of natural science and have important applications in many fields including pharmaceutical research, functional materials and synthetic chemistry. These compounds exhibit a wide range of biological activities, including anti-cancer, anti-inflammatory, anti-bacterial and anti-hypertensive activities, and can also be used in the fields of corrosion inhibitors, surface-active treatment agents and chemiluminescent materials. Because imidazoles have so many uses, the development of efficient strategies to synthesize imidazoles has always attracted the attention of the field of synthetic chemistry. [0003] Isonitriles, an important class of organic molecules...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02
CPCC07D235/02
Inventor 任志林刘玉亭付林和平蔡爽邱继莹
Owner HUBEI UNIV OF ARTS & SCI
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