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6 (aryloxy methyl) - 2 aryl - 6, 7 dihydro 4h - pyrido [5,1 c ] [1,4] oxaxine - 4 - ketone derivative, and preparation method

A technology of derivatives and methyl, which is applied in the field of pyrazoloxazine derivatives and their preparation, and can solve the problems of underreporting of pyrazoloxazine derivatives, etc.

Inactive Publication Date: 2007-05-09
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In terms of structural modification, better biological activity can often be obtained through a reasonable combination of pharmacophore. Literature search shows that there are few reports on pyrazoloxazine derivatives, especially no reports on 6-(aryloxymethyl) -Reports on the structure and synthesis method of 2-aryl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-4-one derivatives or related content

Method used

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  • 6 (aryloxy methyl) - 2 aryl - 6, 7 dihydro 4h - pyrido [5,1 c ] [1,4] oxaxine - 4 - ketone derivative, and preparation method
  • 6 (aryloxy methyl) - 2 aryl - 6, 7 dihydro 4h - pyrido [5,1 c ] [1,4] oxaxine - 4 - ketone derivative, and preparation method
  • 6 (aryloxy methyl) - 2 aryl - 6, 7 dihydro 4h - pyrido [5,1 c ] [1,4] oxaxine - 4 - ketone derivative, and preparation method

Examples

Experimental program
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Embodiment 1

[0035] Preparation of 6-(phenoxymethyl)-2-phenyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-4-one 1) 3.24 Gram (0.015 mol) 3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester and 2.25 gram (0.015 mol) 3-phenoxyl-1,2-epoxypropane were added in 50 ml of freshly distilled acetonitrile, Add 4.14 g (0.030 moles) of potassium carbonate, and stir and reflux under nitrogen protection for 15 hours. Cool to room temperature, evaporate acetonitrile under reduced pressure, and separate the residue by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=2:1, volume ratio) to obtain 1-(2-hydroxyl-3-phenoxypropane yl)-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (4.91 g), the yield was 89.5%.

[0036]2) Add 0.168 g ( 0.003 mole) of potassium hydroxide, stirred and refluxed for 3 hours. Cool to room temperature, distill off ethanol under reduced pressure, dissolve the residue in 40 ml of water, adjust the pH to 4-5 with 10% hydrochloric acid solution, p...

Embodiment 2

[0051] 6-((4-chlorophenoxy)methyl)-2-phenyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-4-one preparation

[0052] 1) Add 3.24 grams (0.015 moles) of 3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester and 2.77 grams (0.015 moles) of 3-(4-chlorophenoxy)-1,2-epoxypropane Add 3.18 g (0.030 mol) of sodium carbonate to 50 ml of freshly distilled acetonitrile, and stir and reflux for 15 hours under nitrogen protection. Cool to room temperature, evaporate acetonitrile under reduced pressure, and the residue is separated by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=2:1, volume ratio) to obtain 1-(3-(4-chlorophenoxy )-2-Hydroxypropyl)-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (4.78 g), yield 79.5%.

[0053] 2) 0.801 g (0.002 mol) of 1-(3-(4-chlorophenoxy)-2-hydroxypropyl)-3-phenyl-1H pyrazole-5-carboxylic acid ethyl ester in ethanol (20 ml) 0.120 g (0.003 mol) of sodium hydroxide was added into the solution, and the mixture was stir...

Embodiment 3

[0068] 6-((4-nitrophenoxy)methyl)-2-phenyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine-4- Preparation of ketones

[0069] 1) Mix 3.24 grams (0.015 moles) of ethyl 3-phenyl-1H-pyrazole-5-carboxylate with 2.93 grams (0.015 moles) of 3-(4-nitrophenoxy)-1,2-propylene oxide Added to 50 ml of freshly distilled acetonitrile, then added 4.14 g (0.030 mol) of potassium carbonate, stirred and refluxed for 18 hours under nitrogen protection. Cool to room temperature, evaporate acetonitrile under reduced pressure, and the residue is separated by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=2:1, volume ratio) to obtain 1-(2-hydroxyl-3-(4- Nitrophenoxy)propyl)-3-phenyl-1H-pyrazole-5-carboxylic acid ethyl ester (4.72 g), yield 76.6%.

[0070] 2) in 0.822 gram (0.002 mol) 1~(2-hydroxyl-3-(4-nitrophenoxy group) propyl group)-3-phenyl-1H-pyrazole-5-formic acid ethyl ester of ethanol (20 Milliliters) solution was added 0.168 gram (0.003 mol) potassium h...

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Abstract

This invention relates to 6-(aroxylmethyl)-2-aryl-6,7-dihydrogen-4H-pyrazole[5,1-c][1,4]oxazine-4-ketone derivatives with a general structure shown in formula I, where, X and Y are H, linear or branched C1-4 alkyl, alkoxyl, halogen or nitryl. This invention also relates to the method for preparing the compounds, which comprises: mixing 3-aroxyl-1,2-epoxypropane, 3-aryl-1H-pyrazole-5-ethyl formate and K2CO3 acid captor, and refluxing in acetonitrile to obtain 1-(2-hydroxyl-3-aroxylpropyl)-3-aryl-1H-pyrazole-5-ethyl formate derivatives, hydrolyzing in alcohol solvent in an alkaline condition to obtain 1-(2-hydroxyl-3-aroxylpropyl)-3-aryl-1H-pyrazole-5-formic acid derivatives, and lactonizing under the catalysis of acid to obtain the products.

Description

field of invention [0001] The present invention relates to pyrazolooxazine derivatives and a preparation method thereof, in particular to 6-(aryloxymethyl)-2-aryl-6,7-dihydro-4H-pyrazolo[5,1-c] [1,4]Oxazin-4-one derivatives and methods for their synthesis, separation and purification. Background technique [0002] Pyrazole derivatives and 2-morpholinone derivatives are two very important compounds that have received extensive attention in the development of new drugs. These compounds have anti-inflammatory, analgesic, antipyretic, bacteriostatic, bactericidal, anti-hyperglycemic, and anti-cancer properties. , anticoagulant and other pharmacological activities. For example, the pyrazole derivatives described in JP5017470, U.S.5134142, and WO96 / 03385 have anti-inflammatory, anti-rheumatic, anti-bacterial, and anti-viral pharmacological activities. The patent No. is U.S.3984431. The structure of the involved pyrazole-5-acetic acid, especially 1-tert-butyl-3,4-diphenyl-1H-pyraz...

Claims

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Application Information

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IPC IPC(8): C07D498/04
Inventor 赵宝祥韦芳董文亮
Owner SHANDONG UNIV
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