2-(2,6-dicyanophenyl)imidazo[1,2-α]pyridine compounds and preparation method thereof

A technology of dicyanophenyl and imidazolium, which is applied in the field of organic compound synthesis and application, can solve the problems such as few reports of pyridoimidazole, and achieve the effects of anti-apoptotic biological activity and anti-viral biological activity.

Active Publication Date: 2018-12-14
ZHENGZHOU UNIV
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  • Abstract
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  • Application Information

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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 nitrile reaction of pyridoimidazole

Method used

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  • 2-(2,6-dicyanophenyl)imidazo[1,2-α]pyridine compounds and preparation method thereof
  • 2-(2,6-dicyanophenyl)imidazo[1,2-α]pyridine compounds and preparation method thereof
  • 2-(2,6-dicyanophenyl)imidazo[1,2-α]pyridine compounds and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0021] Compound 2-(2,6-dicyanophenyl)imidazo[1,2- α ] The structural formula of pyridine is:

[0022]

[0023] The preparation method is: add 0.1 mmol of 2-phenylimidazo[1,2- α ] pyridine compound, 0.25 mmol of N-cyano-N-phenyl-p-toluenesulfonamide, 0.005 mmol of dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, 0.04 mmol of Silver hexafluoroantimonate, 0.05 mmol of sodium bicarbonate and 1 mL of 1,2-dichloroethane, 120 o C was reacted for 24 hours. After the reaction, 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 89%, melting point: 208-209 o c. 1 HNMR (400 MHz, CDCl 3 ) δ 8.21 (d, J = 6.9 Hz, 1H), 8.19 (s, 1H), 8.00 (d, J =7.9 Hz, 2H), 7.73 (d, J = 9.2 Hz, 1H), 7.57 (t, J = 15.7 Hz, 1H), 7.26-7.30(m, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 145.3, 140.6, 138.2, 137.8, 128.4, 126.1, 125.9, 118.5, 117.4, 113.8, 113.6, 112.9...

Embodiment 2

[0025] Compound 2-(4-methyl-2,6-dicyanophenyl)imidazo[1,2- α ] The structural formula of pyridine is:

[0026]

[0027] The preparation method is: add 0.1 mmol of 2-(4-methylphenyl)imidazo[1,2- α ] pyridine compound, 0.1 mmol of N-cyano-N-phenyl p-toluenesulfonamide, 0.0001 mmol of dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, 0.01 mmol of Silver hexafluoroantimonate, 0.01 mmol of sodium bicarbonate and 1.5 mL of 1,2-dichloroethane, 120 o C was reacted for 24 hours. After the reaction, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), and drying to obtain a light yellow solid with a yield of 70%. Melting point: 205-206 o c. 1 H NMR (400 MHz, CDCl 3 ) δ 8.19 (dd, J = 0.9, 1 Hz, 1H), 8.15 (s,1H), 7.79 (s, 2H), 7.72 (d, J = 9.2 Hz, 1H),7.24-7.28 (m, 1H),6.86-6.89 (m,1H). 13C NMR (151 MHz, CDCl 3 ) δ 145.3, 139.2, 138.3, 138.2, 137.8, 126.0, 125.8, 118.4, 117.5, 11...

Embodiment 3

[0029] Compound 2-(4-ethyl-2,6-dicyanophenyl)imidazo[1,2- α ] The structural formula of pyridine is:

[0030]

[0031] The preparation method is: add 0.1 mmol of 2-(4-ethylphenyl)imidazo[1,2- α ] pyridine compound, 0.4 mmol of N-cyano-N-phenyl-p-toluenesulfonamide, 0.001 mmol of dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, 0.08 mmol of Silver hexafluoroantimonate, 0.15 mmol of sodium bicarbonate, 3 mL of 1,2-dichloroethane, 120 o C was reacted for 24 hours. After the reaction, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), and drying to obtain a light yellow solid with a yield of 86%. Melting point: 175-178 o c. 1 H NMR (400 MHz, CDCl 3 ) δ 8.2 (dt, J = 6.8, 1.1 Hz, 1H), 8.1 (s, 1H),7.8 (s, 2H), 7.7 (d, J = 9.2 Hz, 1H), 7.3 (m, 1H), 6.9 (td, J = 6.8, 1.0 Hz,1H), 2.8 (q, J = 7.6 Hz, 2H), 1.32(t, J = 7.6 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 145.3, 145.2...

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Abstract

The invention discloses a 2-(2,6-dicyanophenyl) imidazo [1,2-alpha] pyridine compound obtained through a direct nitrile grouping reaction method of a 2-phenyl-imidazo [1,2-alpha] pyridine compound and N-cyan-N-phenyl p-methylphenyl sulphonylamine (NCTS). The reaction is characterized by utilizing dichloro (pentamethyl cyclopentadienyl) rhodium (III) dimer ([RhCp*Cl2]2) and silver hexafluoroantimonate (AgSbF6) as catalysts, adopting sodium bicarbonate (NaHCO3) as an additive, adopting 1,2-dichloroethane as a reaction solvent, and realizing nitrile grouping reaction of the 2-phenyl-imidazo [1,2-alpha] pyridine compound and the N-cyan-N-phenyl p-methylphenyl sulphonylamine (NCTS). The method is simple and efficient, a functionalization reaction type of the 2-phenyl-imidazo [1,2-alpha] pyridine compound is enriched, and meanwhile, a new reaction mode of the N-cyan-N-phenyl p-methylphenyl sulphonylamine (NCTS) is also realized. The method has significance on research and application of nitrile grouping reaction of the 2-phenyl-imidazo [1,2-alpha] pyridine compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, in particular to a 2-(2,6-dicyanophenyl)imidazo[1,2- α ] The preparation method of pyridine compound. Background technique [0002] Contains imidazo[1, 2- α ] The organic compound of the pyridine molecular skeleton is a very important and common organic heterocyclic compound, and the substituted imidazo[1, 2- α ] Pyridine compounds and their derivatives have good biological activities: for example, antifungal, anti-inflammatory, anticancer, antiviral and antiapoptotic, etc. ( J. Med. Chem. 2015, 58, 8529; Bioorg. Med. Chem. Lett. 2013, 23, 4996; J. Med. Chem . 2015, 58, 9238; Bioorg. Med. Chems . 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 Alpidem (anti-anxiety agent), Saripidem (sedative drug), Necopidem (anesthetic drug) and Zolpidem (se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 宋冰朱新举申晓静刘文博刘春玉赵雪梅郝新奇
Owner ZHENGZHOU UNIV
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