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3-(Benzenesulfonylmethyl)imidazoheterocyclic compounds and synthetic method thereof

A technology of benzenesulfonylmethyl and benzenesulfonylmethyl isonitrile, which is applied in the field of organic compound synthesis and application, can solve problems such as unreported sulfonyl methylation reaction, and achieve the effect of enriching functional group reaction types

Active Publication Date: 2018-09-04
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on the functionalization reaction of pyridoimidazole compounds and imidazoheterocyclic compounds is becoming more and more perfect, but there is no report on the research on the sulfonylmethylation reaction.

Method used

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  • 3-(Benzenesulfonylmethyl)imidazoheterocyclic compounds and synthetic method thereof
  • 3-(Benzenesulfonylmethyl)imidazoheterocyclic compounds and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Compound 2-(furan-2-yl)-3-(tosylmethyl)imidazo[1,2- a ] The structure of pyridine is:

[0025] ;

[0026] Preparation method: Add 0.1 mmol of 2-furylimidazo[1,2-a]pyridine compound, 0.2 mmol of p-toluenesulfonylmethyl isocyanide, 0.02 Mmol of ferric chloride, 2 mL of water, react at 100°C for 36 hours; after the reaction, extract with dichloromethane, concentrate under reduced pressure and then chromatographically separate (silica gel 200-300 mesh), eluent: ethyl acetate / petroleum Gradient elution with ether, the ratio is from 0 / 100 to 100 / 0), and drying to obtain a white solid with a yield of 90%. m.p. = 163-164°C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.40 (d, J = 6.9 Hz, 1H), 7.60(d, J = 9.1 Hz, 1H), 7.38 (d, J = 8.2 Hz, 2H), 7.32-7.29 (m, 1H), 7.13 (dd , J= 1.6, 0.5 Hz, 1H), 7.06 (d, J = 7.9 Hz, 2H), 6.94 (td, J = 6.8, 1.0 Hz, 1H), 6.66 (d, J = 1.1 Hz, 1H), 6.31 (dd, J = 3.4, 1.8 Hz, 1H), 5.08 (s, 2H), 2.27(s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 149.1, 146.3, 145.1,...

Embodiment 2

[0028] Compound 2-(thiophen-2-yl)-3-(tosylmethyl)imidazo[1,2- a ] The structure of pyridine is:

[0029] ;

[0030] Preparation method: Add 0.1 mmol of 2-thienylimidazo[1,2-a]pyridine compound, 0.3 mmol of p-toluenesulfonylmethyl isocyanide, 0.03 Mmol of ferric chloride, polyethylene glycol 400 2mL, react at 100°C for 18 hours; after the reaction, extract with dichloromethane, concentrate under reduced pressure and then chromatographically separate (silica gel 200-300 mesh), eluent: ethyl acetate Gradient elution with ester / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 87%. m.p. = 161-162°C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.33 (d, J = 6.9 Hz, 1H),7.64 (d, J = 9.1 Hz, 1H), 7.50 (d, J = 8.3 Hz, 2H), 7.31-7.26 (m, 2H), 7.15(d , J = 8.0 Hz, 2H), 7.02 (dd, J = 3.6, 1.0 Hz, 1H), 6.95 (dd, J = 5.0, 3.7Hz, 1H), 6.90 (td, J = 6.8, 1.0 Hz, 1H) , 4.90 (s, 2H), 2.35 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 146.0, 145.5, 141.7, ...

Embodiment 3

[0032] The compound 6-phenyl-5-(tosylmethyl)imidazo[2,1- b ] The structural formula of thiazole is:

[0033] ;

[0034] Preparation method: Add 0.1 mmol of 6-phenylimidazo[2,1- b ] Thiazole compound, 0.3mmol of p-toluenesulfonylmethyl isonitrile, 0.01mmol of iron trichloride, water and polyethylene glycol 400 (volume ratio 7:3) 2 mL, 120 ℃ of reaction 24 hours; , extracted with dichloromethane, concentrated under reduced pressure and then chromatographically separated (silica gel 200-300 mesh), eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), and dried to obtain a white solid , 85% yield. m.p. = 39-40℃. 1 H NMR (600 MHz, CDCl 3 ) δ 7.71 (d, J = 4.5Hz, 1H), 7.45 (d, J = 8.2 Hz, 2H), 7.24-7.23 (m, 3H), 7.18-7.14 (m, 4H), 6.90(d, J = 4.5 Hz, 1H), 4.69 (s, 2H), 2.37 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ150.9, 148.7, 145.4, 134.1, 133.2, 129.9, 128.29, 128.27, 127.8, 127.6, 119.1, 112.6, 109.8, 53.6, 21.6. HRMS (positive ESI): [M+H] + ...

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Abstract

The invention discloses a 2-heteroaryl-3-(toluenesulfonyl methyl)imidazo heterocyclic compound and a synthesis method thereof. The method includes the following steps that in an argon environment, a 2-heteroaryl-imidazo heterocyclic compound and tosylmethyl isocyanide are added into a reaction tube, ferric trichloride is added, then a green solvent is added, and the mixture is subjected to a reaction for 18-48 hours at the temperature of 80-120 DEG C; after the reaction is ended, the target product is obtained through extraction, chromatographic separation and drying. In the reaction, cheap metallic iron (III) is utilized as a catalyst, water and polyethylene glycol400 are used as a reaction solvent, in this way, the sulfonyl methylation reaction between the imidazo heterocyclic compound and tosylmethyl isocyanide is achieved, sulfonyl of the obtained compound can serve as a leaving group to further achieve a functional group reaction, and the method will have important meaning for research and application of the sulfonyl methylation reaction of the imidazo heterocyclic compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and in particular relates to a preparation method of 3-(benzenesulfonylmethyl) imidazoheterocyclic compounds. Background technique [0002] Pyridoimidazole is a very important and common nitrogen heterocyclic compound (ComprehensiveHeterocyclic Chemistry III). Its derivatives have good biological activity: for example, antiviral, antiulcer and antibacterial properties (J. Med. Chem. 2015, 58, 8529; Bioorg. Med. Chem. Lett. 2013, 23, 4996; J. Med. 2015, 58, 9238; Bioorg. Med. Chem. 2011, 19, 4227; ACS Med. Chem. Lett. 2013, 4, 675; J. Med. Chem. 1999, 42, 50). Among them, several types of drugs have been successfully marketed, such as anti-anxiety drugs Alpidem (Alpidem), Saripidem (Saripidem), anesthetic drugs Necopidem (Necopidem) and sedative hypnotics Zolpidem (Zolpidem), etc. ( J. Med. Chem. 2008, 51, 7243; Exp. Ther. 2001, 299, 793; J. Behav. Pharmaco...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D409/04C07D513/04C07D487/04
CPCC07D405/04C07D409/04C07D487/04C07D513/04
Inventor 朱新举卢帅李科田子瑶碗晓敏郝新奇赵雪梅宋毛平
Owner ZHENGZHOU UNIV
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