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A kind of synthetic method of pyridoxazole derivative

A synthetic method and derivative technology, applied in the direction of organic chemistry, etc., to achieve the effects of simple preparation, high yield, and convenient operation

Active Publication Date: 2021-04-16
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of synthesizing pyridoxazoles under the catalytic system of copper and 2,2,6,6-tetramethylpiperidine-1-oxyl radical has not been reported in the literature

Method used

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  • A kind of synthetic method of pyridoxazole derivative
  • A kind of synthetic method of pyridoxazole derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]Synthesis of 2-phenylpyridine and oxazole

[0018]5.40 g (48.8 mmol) of 2-amino 3-hydroxypyridine and 5.0 g (48.8 mmol) of benzomethaldehyde, 60 ml of acetonitrile or methanol were added as a solvent, and stirred at 80oC, and then under the oxygen atmosphere 0.50 g (5 mmol) of copper chloride, 1.44 g (10 mmol) 2,2,6,6-tetramethylpiperidine-1-oxygen free radical, 1.80 g (10 mmol) adjacent firioline added to the reaction solution After heating and reflow, after the reaction is stopped, the cooled, adding the alkali, the filter, the crude product is thin layer chromatography (petroleum ether: ethyl acetate = 5-10: 1) Separate white solid 2-phenylpyridine And oxazole, melting point: 132 ° C ~ 134oC. Yield (yield): 8.81 g (92.2%). Character data:1H NMR (400 MHz, CDCL3: δ = 8.58 (D, 1H), 8.34-8.31 (m, 2H), 7.88-7.86 (m, 1H), 7.61-7.53 (m, 3H), 7.31-7.28 (m, 1H). EI-MS (m / z): 196.

Embodiment 2

[0020]Synthesis of 2- (4-methoxy) phenylpyridine and oxazole

[0021]5.40 g (48.8 mmol) of 2-amino 3-hydroxypyridine and 6.60 g (48.8 mmol) were added to 6.60 g (48.8 mmol) of methoxybenzoladehyde, 60 ml acetonitrile as a solvent, stirred at 80oC, and then in an oxygen atmosphere 0.50 g (5 mmol) chloride, 1.44 g (10 mmol) 2,2,6,6-tetramethylpiperidine-1-oxygen free radical, 1.80 g (10 mmol) adjacent to the reaction solution In the heat generation, the reaction is stopped, the reaction is stopped, the alkali is neutralized, filtered, the crude product is thin layer chromatography (petroleum ether: ethyl acetate = 5-10: 1) Separate white solid 2- (4 - Methoxy) phenylpyridine and oxazole, melting point: 136.6-139.3oC. Yield (yield): 9.47 g (90.7%). Character data:1H-NMR (400 MHz, CDCL3: δ = 8.52-8.50 (m, 1H), 8.25-8.7 (M, 2H), 7.02-7.20 (M, 1H), 7.02-7.00 (m, 2H), 3.87 (S, 3H). EI-MS (M / Z): 214.

Embodiment 3

[0023]Synthesis of 2- (4-fluorine) phenylpyridine and oxazole

[0024]5.40 g (48.8 mmol) of 2-amino 3-hydroxypyridine and 6.0 g (48.8 mmol) were added to 6.0 g (48.8 mmol) of fluorobenzaldehyde, 60 ml acetonitrile as a solvent, and stirred under 90oC, then under the oxygen atmosphere 0.50 g (5 mmol) of copper chloride, 1.44 g (10 mmol) 2,2,6,6-tetramethylpiperidine-1-oxygen free radical, 1.80 g (10 mmol) adjacent feline added to the reaction solution, After heating and reflow, the reaction is stopped, cooled, in the alkali, filtration, crude product with thin layer chromatography (Oil ether: ethyl acetate = 5-10: 1) Separate white solid 2- (4-fluorine Phenylpyridine and oxazole, melting point: 129.4-133.5oC. Yield (yield): 9.29 g (94.2%). Character data:1H-NMR (400 M, 1H), 7.20-7.21 (m, 1H), 7.24-7.21 (m, 1H), 7.20-7.14 (M, 1H), 7.20-7.14 (M, 1H), 7.20-7.14 , 2H), PPM. Ei-ms (m / z): 202.

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Abstract

The invention provides a synthetic method of pyridoxazole derivatives, which comprises the following steps: dissolving 2-amino 3-hydroxypyridine and aldehyde in an organic solvent, stirring at 70-90°C for 2-3h, and then under an oxygen atmosphere 2,2,6,6-tetramethylpiperidine-1-oxyl radical, cuprous chloride and o-phenanthroline were added to the reaction solution, and after the reaction was completed, the organic solvent was removed, and the residue was thinned The pyridoxazole derivatives can be obtained through layer chromatography separation. The present invention utilizes copper and 2,2,6,6-tetramethylpiperidine-1-oxyl radical system to catalyze the reaction of synthesizing 2-substituted oxazolopyridines, compared to known catalytic methods, the invention has the following Advantages: convenient operation, low cost and high yield; simple and efficient catalyst preparation; the catalytic process is green and environmentally friendly.

Description

Technical field[0001]The present invention relates to the field of organic synthesis, and more particularly to a method of synthesizing pyridine and oxazole derivatives.Background technique[0002]Pyridine and oxazole compounds are a kind of active heterocyclic compound having broad-spectrum activity in the pharmaceutical field, with biological characteristics such as pain, bactericidal, anti-inflammatory, analgesic, treatment of sleep disorders and their extensive application prospects. Studies have shown that electron donors with large-range conjugate structures can effectively improve the light-emitting performance and coordination properties of the photosensitive material, so development pyridine and oxazole compounds are very important in pharmacology, agricultural and industrial sectors. Significance, therefore become one of the research hotspots in today's chemical community.[0003]Through the literature, the proprioxazole compound existing synthesis method has a more expensive ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 刘娥王洪林李立威
Owner JINGCHU UNIV OF TECH