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2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and synthetic method thereof

A technology of toluenesulfonylmethyl and p-toluenesulfonylmethyl isonitrile is applied in the field of organic compound synthesis and application, and can solve the problems of rarely reported pyridoimidazole sulfonylmethylation reaction and the like

Active Publication Date: 2017-01-04
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 pyridoimidazole has become more and more mature, but there are few reports on the sulfonylmethylation reaction of pyridoimidazole

Method used

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  • 2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and synthetic method thereof
  • 2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and synthetic method thereof
  • 2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and synthetic method thereof

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Experimental program
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Embodiment 1

[0024] The structural formula of the compound 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine in this example is:

[0025]

[0026] The preparation method is: under argon protection, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.2mmol of p-toluenesulfonyl methyl isocyanide, 0.02 to 10mL Shrek tube 1 mmol of ferric chloride, water and polyethylene glycol 400 (volume ratio 1:1) 2 mL, reacted at 90°C for 24 hours; after the reaction, it was extracted with dichloromethane, concentrated under reduced pressure and chromatographed (silica gel 200-300 Mesh, eluent: ethyl acetate / petroleum ether gradient elution, the ratio is from 0 / 100 to 100 / 0), dried to obtain a white solid, the yield is 94%. m.p.=68-69°C. 1 H NMR(600MHz, CDCl 3 )δ8.45(d,J=6.8Hz,1H), 7.67(d,J=8.9Hz,1H), 7.38(d,J=8.1Hz,2H),7.33-7.27(m,6H), 7.09( d, J = 8.0 Hz, 2H), 6.94 (t, J = 6.7 Hz, 1H), 4.87 (s, 2H), 2.36 (s, 3H). 13 C NMR(150MHz, CDCl 3 )δ147.5,146.0,145.3,134.2,133.0,129.8,128.3,128.22,128.16,128.1,126...

Embodiment 2

[0028] The structural formula of the compound 2-(o-tolyl)-3-(tosylmethyl)imidazo[1,2-a]pyridine in this embodiment is:

[0029]

[0030] The preparation method is as follows: Add 0.1mmol of 2-o-tolylimidazo[1,2-a]pyridine compound and 0.3mmol of p-toluenesulfonylmethyl isocyanide into a 10mL Shrek tube under an argon atmosphere. 0.03mmol of ferric chloride, 2mL of water, reacted at 110°C for 22 hours; after the reaction, it was extracted with dichloromethane, concentrated under reduced pressure and chromatographed (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether Gradient elution, the ratio is from 0 / 100 to 100 / 0), dried to obtain a white solid with a yield of 89%. m.p.=133-134°C. 1 H NMR(600MHz, CDCl 3 )δ8.53(d,J=7.5Hz,1H), 7.63(d,J=9Hz,1H),7.33-7.29(m,3H), 7.21(t,J=7.5Hz,1H), 7.13(d ,J=8.3Hz,1H),7.11(d,J=7.9Hz,2H),7.02(t,J=7.4Hz,1H),6.95(td,J=6.8,0.8Hz,1H),6.69(d ,J=7.0Hz,1H),4.72(s,2H),2.40(s,3H),1.99(s,3H). 13 C NMR(150MHz, CDCl 3 )δ147.9,145.7,145.0,137.3,134...

Embodiment 3

[0032] The structural formula of the compound 2-(3-methoxyphenyl)-3-(tosylmethyl)imidazo[1,2-a]pyridine of this embodiment is:

[0033]

[0034] The preparation method is: under argon protection, add 0.1mmol of 2-(3-methoxyphenyl)imidazo[1,2-a]pyridine compound and 0.3mmol of p-toluenesulfonate to 10mL Shrek tube Acylmethyl isonitrile, 0.02mmol ferric chloride, 2mL of water and polyethylene glycol 400 (volume ratio 2:1), reacted at 100°C for 36 hours; after the reaction, it was extracted with dichloromethane and concentrated under reduced pressure Chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), dried to obtain a white solid, yield 98%. m.p.=173-174℃. 1 H NMR(600MHz, CDCl 3 )δ8.42(d,J=6.8Hz,1H), 7.65(d,J=9.0Hz,1H), 7.40(d,J=8.2Hz,2H), 7.31-7.29(m,1H), 7.19( t,J=7.9Hz,1H),7.10(d,J=8.1Hz,2H),6.96(s,1H),6.93-6.89(m,2H),6.84(dd,J=8.2,2.2Hz,1H ), 4.88(s, 2H), 3.82(s, 3H), 2.36(s, 3H). 13 C NMR(15...

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Abstract

The invention discloses a 2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and a preparation method thereof. The preparation method comprises the following steps: adding 2-phenyl-imidazo [1,2-a] pyridine compound and p-tolylsulfonylmethyl isocyanide into a reaction tube in an argon environment, adding ferric trichloride, then adding a green solvent, and reacting for 18 to 48 hours at 80 to 120 DEG C; and after the reaction, extracting, chromatographically separating, and drying to obtain a target product. In the reaction, cheap metal ion (III) is used as a catalyst, water and polyethylene glycol 400 are used as reaction solvents, the sulfonylmethylation reaction of the imidazo [1,2-a] pyridine compound and p-tolylsulfonylmethyl isocyanide is realized, sulfonyl of the obtained compound is used as a leaving group, and the further functional group reaction is realized. The method has important significance on the research and application of the sulfonylmethylation 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 specifically relates to a preparation method of 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compounds. Background technique [0002] Pyridinoimidazole is a very important and common nitrogen heterocyclic compound (Comprehensive Heterocyclic Chemistry III). Its derivatives have good biological activities: for example, antiviral, antiulcer and antibacterial properties (J.Med.Chem.2015,58,8529; Bioorg.Med.Chem.Lett.2013,23,4996; J.Med .Chem.2015,58,9238; Bioorg.Med.Chem.2011,19,4227; ACS Med.Chem.Lett.2013,4,675; J.Med.Chem.1999,42,50). Several types of drugs have been successfully marketed, such as the anti-anxiety drugs Alpidem (Alpidem), Saripidem (Saripidem), the anesthetic Necopidem (Necopidem), and the sedative and hypnotic Zolpidem (Zolpidem). J. Med. Chem. 2008, 51, 7243; Exp. Ther. 2001, 299, 793; J. Behav. Pharmacol. 1995, 6, 116). In recent years, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 朱新举卢帅杨发琉郭玉静田子瑶郝新奇赵雪梅宋毛平
Owner ZHENGZHOU UNIV
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