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N-(2-arylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonylimide compound and its synthesis method

A technology of bisbenzenesulfonimide and arylimidazolium is applied in the field of preparation of N-bisbenzenesulfonimide compounds, and can solve the problems such as few reports of pyridoimidazole sulfonamidation reaction

Active Publication Date: 2020-06-05
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research on the functionalization reaction of imidazopyridine compounds has become more and more mature, but there are few reports on the sulfonamidation reaction of pyridoimidazoles

Method used

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  • N-(2-arylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonylimide compound and its synthesis method
  • N-(2-arylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonylimide compound and its synthesis method
  • N-(2-arylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonylimide compound and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The structural formula of the compound N-(2-phenylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonimide of this embodiment is:

[0024]

[0025] The preparation method is: in the air environment, add 0.2mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.6mmol of N-fluorobisbenzenesulfonimide, 0.02mmol into a 15mL high-pressure reaction tube Tetraacetonitrile copper (I) tetrafluoroborate, dichloroethane 2mL, react at 90°C for 6 hours; Rinse, the ratio is from 0 / 100 to 100 / 0), and dry to obtain a light yellow solid with a yield of 94%. m.p. = °C. 1 HNMR (600MHz, CDCl 3 )δ7.92(d, J=7.9Hz, 4H), 7.72(d, J=7.7Hz, 2H), 7.64(d, J=8.9Hz, 1H), 7.58(t, J=7.4Hz, 2H) ,7.51(d,J=6.8Hz,1H),7.40(t,J=7.7Hz,4H),7.29-7.28(m,1H),7.17(t,J=7.3Hz,1H),7.11(t, J=7.6Hz, 2H), 6.65(t, J=6.8Hz, 1H). 13 C{ 1 H}NMR (150MHz, CDCl 3 )δ145.6, 144.5, 139.1, 134.6, 131.8, 129.1, 129.0, 128.4, 128.1, 127.5, 126.8, 123.9, 118.0, 112.6, 111.1. HRMS (positive ESI): [M+H] + calcd for C 25 h 20 N 3 o 4 ...

Embodiment 2

[0027] The structural formula of the compound N-(2-o-tolyl-imidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonimide of this embodiment is:

[0028]

[0029] The preparation method is: in an air environment, add 0.2mmol of 2-o-tolyl imidazo[1,2-a]pyridine compound, 0.3mmol of N-fluorobisbenzenesulfonimide, 0.24 Mmol tetraacetonitrile copper (I) tetrafluoroborate, dichloroethane 2mL, react at 110°C for 6 hours; Gradient elution, ratio from 0 / 100 to 100 / 0), drying to obtain a yellow solid with a yield of 89%. m.p.=193-194°C. 1 H NMR (600MHz, CDCl 3 )δ7.78(d, J=7.3Hz, 4H), 7.64-7.56(m, 4H), 7.45(d, J=7.0Hz, 1H), 7.36(t, J=7.0Hz, 4H), 7.28- 7.26(m, 1H), 7.19(t, J=7.0Hz, 1H), 7.09(d, J=7.0Hz, 1H), 7.03(t, J=6.8Hz, 1H), 6.68(t, J=5.6 Hz,1H),2.15(s,3H). 13 C{1H}NMR (150MHz, CDCl 3 )δ147.8, 144.2, 138.9, 138.1, 134.3, 131.4, 130.4, 129.7, 129.0, 128.7, 126.5, 125.1, 124.0, 118.0, 112.7, 111.8, 20.5. HRMS (positive ESI): [M+H] + calcd for C 26 h 22 N 3 o 4 S 2 + :504.1046, found...

Embodiment 3

[0031] The structural formula of the compound N-(2-(3-methoxyphenyl)-imidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonimide in this embodiment is:

[0032]

[0033]The preparation method is: under air environment, add 0.2mmol of 2-(3-methoxyphenyl)imidazo[1,2-a]pyridine compound, 0.6mmol of N-fluorobiphenyl Sulfonimide, 0.02 mmol tetraacetonitrile copper (I) tetrafluoroborate, 1 mL dichloroethane, react at 100 ° C for 6 hours; after the reaction, concentrate under reduced pressure and then chromatographically separate (silica gel 200-300 mesh, eluent: Gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and drying to obtain a white solid with a yield of 77%. m.p.=160-161°C. 1 H NMR (600MHz, CDCl 3 )δ7.92(d, J=7.6Hz, 4H), 7.64(d, J=8.9Hz, 1H), 7.58(t, J=7.2Hz, 2H), 7.47(d, J=6.5Hz, 1H) ,7.40(t,J=7.4Hz,4H),7.36-7.35(m,2H),7.28-7.27(m,1H),7.06(t,J=7.7Hz,1H),6.74(d,J=8.0 Hz,1H),6.65(t,J=6.2Hz,1H),3.69(s,3H). 13 C{ 1 H}NMR (150MHz, CDCl 3 )δ159...

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Abstract

The invention discloses an N-(2-arylimidazo[1,2-a]pyridine-3-yl)bisbenzenesulfonimide compound and a synthetic method thereof. The synthetic method comprises the following steps: adding a 2-aryl-imidazo[1,2-a]pyridine compound and N-fluorobisbenzenesulfonimide into a reaction tube in an air environment, adding tetrakiscopper tetrafluoroborate (I), then adding dichloroethane, and carrying out a reaction at 90 to 110 DEG C for 0.1 to 12 hours; and after completion of the reaction, carrying out chromatographic separation and drying so as to obtain a target product. According to the invention, thereaction utilizes cheap metal copper (I) as a promoter and dichloromethane as a reaction solvent; and an amination reacation of an imidazo[1,2-a]pyridine compound with the N-fluorobisbenzenesulfonimide is realized. The method provided by the invention has important significance on research and application of the amination reaction of the imidazo[1,2-a]pyridine compound.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and in particular relates to a preparation method of N-(2-arylimidazo[1,2-a]pyridin-3-yl)bisbenzenesulfonimide compounds. Background technique [0002] Imidazopyridine is a common nitrogen-containing heterocyclic compound in medicinal chemistry (Comprehensive HeterocyclicChemistry III). Its derivatives have good biological activity: for example, antiviral, antifungal, antiulcer and antibacterial properties (Bioorg.Med.Chem.2015,23,6087; J.Med.Chem.2015,58,8529; Bioorg. J. Org. Chem. 2012, 77, 5552; ​​J. Med. Chem. 2015, 58, 9238; Bioorg. Med. Chem. 2011, 19, 4227; J. Med. Chem. 1999, 42, 50). Several classes of drugs have been successfully listed, such as the drug Zolpidem for the treatment of insomnia, the drug Olprinone for the treatment of acute heart failure, the anti-anxiety drug Alpidem and the anesthetic drug Necopidem, etc. (J.Med.Chem.2008,51,7243; Exp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 朱新举卢帅崔天巍支昌磊赵雪梅郝新奇宋毛平
Owner ZHENGZHOU UNIV
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