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Method of synthesizing novel pyridino imidazole compound

A technology of pyridoimidazole and synthesis method, applied in directions such as organic chemistry, to achieve the effects of mild reaction conditions, simple and easy-to-obtain reaction raw materials, and reduced use and discharge

Inactive Publication Date: 2013-04-03
SUZHOU UNIV
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Problems solved by technology

[0005] Judging from the existing literature, the most commonly used method is (1) the condensation reaction of 2-aminopyridine and α-halide, (a) J. Org. Chem. 1978, 43, 2900. (b) J. Med. Chem. 1996, 39, 2856. (c) J. Med. Chem. 1998, 41, 5108. (2) Condensation reaction of 2-aminopyridine, aldehyde and isonitrile, (a) J. Org. Chem. 2007, 72, 1013. (b) Synlett 1998, 661. (c) Tetrahedron Lett. 2011, 52, 3191. (3) Copper-catalyzed reactions of 2-aminopyridines, aldehydes and alkynes, (a) Angew. Chem., Int . Ed. 2010, 49, 2743. (b) Tetrahedron Lett. 2010, 51, 4605. (c) Tetrahedron Lett. 2011, 52, 5789. (4) Other reactions, (a) J. Org. Chem. 2011, 76, 7458. (b) J. Org. Chem. 2003, 68, 4935. (c) Chem. Ber. 1990, 123, 327. (d) Tetrahedron Lett. 2006, 47, 2941. (e) Chem. Ber. . 1970, 103, 3811. However, these methods often require pretreatment of the reaction raw materials, or are carried out under harsh conditions, and often have more by-products

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  • Method of synthesizing novel pyridino imidazole compound
  • Method of synthesizing novel pyridino imidazole compound
  • Method of synthesizing novel pyridino imidazole compound

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[0016] A kind of synthetic method of novel pyridoimidazole compound, comprises the following steps:

[0017] Step 1) Mix acetophenone and 2-amino-4-picoline at a ratio of 1:2, react in cuprous iodide, oxygen, boron trifluoride ether, no solvent, at 40°C, TLC detection.

[0018] Step 2) After the reaction is completed, the target product is obtained through column chromatography separation.

Embodiment 1

[0019] Embodiment 1: the synthesis of 7-methyl-2-phenylpyridoimidazole

[0020] Weigh 2 mmol of acetophenone (0.242 g), 4 mmol of 2-amino-4-picoline (0.4325 g), 0.04 mmol of cuprous iodide (0.076 g), and 0.02 mmol of boron trifluoride ether (0.028 g) in In a 25mL Schlenk-tube, stirred at 40°C for 24 hours in an oxygen atmosphere, separated by column chromatography to obtain 0.292g of pure 7-methyl-2-phenylpyridimidazole, with a yield of 70%.

[0021] 7-methyl-2-phenylimidazo[1,2-a]pyridine

[0022] Yield: 70%; Melting point: 166-167°C; Infrared Spectrum (KBr): ν=1643, 1504, 1474, 782, 722; Proton NMR Spectrum (400 MHz, CDCl 3 ) δ 8.40 (d, J = 6.8 Hz, 1H), 8.30 (s, 1H), 7.94 (d, J = 7.6 Hz, 2H), 7.43 (t, J = 7.5 Hz, 2H), 7.35 (s, 1H ), 7.30 (t, J = 7.2 Hz, 1H), 6.74 (d, J = 6.7 Hz, 1H), 2.35 (s, 3H); C NMR spectrum (75 MHz, cdcl 3 ) δ 146.01, 145.28, 135.67, 133.80, 128.65, 127.78, 125.92, 124.77, 115.74, 115.03, 107.52, 77.51, 77.09, 76.66, 21.35.

Embodiment 2

[0023] Embodiment 2: the synthesis of 2-(4-methoxyphenyl)-7-methylpyridoimidazole

[0024] Weigh 2mmol 4-methoxyacetophenone (0.3001g), 4mmol 2-amino-4-picoline (0.4325g), 0.04mmol cuprous iodide (0.076g), 0.02mmol boron trifluoride ether (0.028 g) in 25 mL of Schlenk-tube, stirred at 40 ° C for 24 hours in an oxygen atmosphere, and separated by column chromatography to obtain 0.2452 g of 2-(4-methoxyphenyl)-7-methylpyridimidazole pure product, yield 51%.

[0025] 2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine

[0026] Yield 51%; melting point: 160-161 ℃; infrared spectrum (KBr): ν=1643, 1609, 1552, 1487, 1246, 1176, 783; nuclear magnetic resonance spectrum (400 MHz, DMSO) δ 7.97 (d, J = 6.6 Hz, 1H), 7.87 (d, J = 8.2 Hz, 2H), 7.69 (s, 1H), 7.38 (s, 1H), 6.96 (d, J = 8.2 Hz, 2H), 6.60 (d, J = 6.4 Hz, 1H), 3.85 (s, 3H), 2.39 (s, 3H); C NMR (75 MHz, cdcl 3 ) δ 159.44, 145.82, 145.01, 135.64, 127.18, 126.35, 124.70, 115.43, 114.92, 114.06, 106.64, 77.51, 77.08, 76.66, 5...

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Abstract

The invention discloses a method of synthesizing a novel pyridino imidazole compound. The method comprises the following steps of: mixing acetophenone and 2-amino-4-picoline with the ratio of 1:2, carrying out reaction with copper iodide, oxygen and boron trifluoride diethyl etherate in the absence of a solvent at the temperature of 40 DEG C, carrying out TLC (Thin Layer Chromatography) detection, and carrying out column chromatography isolation to obtain a target product. According to the technical scheme of the invention, the solvent does not need to be added, so that using and discharging of an organic solvent are reduced; initial raw materials are cheap and easy to obtain, so the synthesis cost is saved; the catalysis condition is simple; and the method is carried out at low temperature, so that the reaction condition is mild.

Description

technical field [0001] The invention relates to a method for synthesizing novel pyridoimidazole compounds. Background technique [0002] Pyridoimidazoles are an important class of nitrogen-containing heterocyclic organic compounds, and their skeletons are widely found in many biologically active drug molecules[(a) Couty, F.; Evano, G. In Comprehensive Hetero-cyclic Chemistry III; Katritzky , A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 11, p 409. (b) Bartholini, G. L.E.R.S. Monograph Ser. 1993, 8,1.]. [0003] Pyridoimidazole compounds are widely used in biomedicine, such as GSK812397 (Ⅰ) (anti-AIDS backup drug, Gudmundsson, K.; Boggs, S. D. PCT Int. Appl. WO 2006026703, 2006; CAN 2006, 144, 274 .); Zolimidine (Ⅱ) (anti-inflammatory, anti-ulcer drug, Enguehard-Gueiffier, C.; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888.); Alpidem (Ⅲ) (anti-anxiety drug, (a) Berson, A.; Descatoire, V.; Sutton, A.; Fau, D.; Maulny, B.; Vad...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 纪顺俊汪顺义蔡忠建
Owner SUZHOU UNIV