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A preparing method of tetrahydro benzopyran derivatives

A technology of benzopyran derivatives and tetrahydrogen, applied in directions such as organic chemistry, can solve the problems such as difficult to obtain substrate, long reaction route, reaction temperature of toxic solvent, etc., and achieves simple operation, short process route and low cost. Effect

Inactive Publication Date: 2015-08-12
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have their own advantages, there are still obvious disadvantages, such as long reaction routes, difficult access to substrates, use of toxic solvents and high reaction temperatures, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Weigh 106 mg (1.0 mmol) of benzaldehyde into a 25 mL single-necked bottle, add 5 mL of water, stir and mix, then add 69.3 mg (1.05 mmol) of malononitrile, 147 mg (1.05 mmol) of dimedone ), β-cyclodextrin 22.7 mg (0.02 mmol) was stirred at 25°C, reacted for about 5 hours, TLC detected that there was no raw material, a large amount of white solid was precipitated in the reaction solution, filtered under reduced pressure to obtain a white powdery solid, silica gel column chromatography Purification, petroleum ether / ethyl acetate system elution (petroleum ether:ethyl acetate volume ratio is 10:1), evaporated to dryness under reduced pressure to obtain the product 2-amino-3-cyano-4-phenyl-7,7 -Dimethyl-5-oxo-5,6,7,8-tetrahydro-4 H - Benzopyran 280 mg, yield 95%;

[0016] Product structure characterization:

[0017] Melting point: 230-235°C; IR (KBr) cm -1 : 3403 (NH 2 ), 2962(C-H), 2216(CN), 1677(C=O), 1664(C=C), 1593(C=C); 1 H NMR (500 MHz, DMSO-d 6 ): δ 7.27 (t, J =7...

Embodiment 2

[0019] Weigh 120 mg (1.0 mmol) of p-tolualdehyde into a 25 mL single-necked bottle, add 5 mL of ethanol, stir and mix, then add 69.3 mg (1.05 mmol) of malononitrile and 147 mg of dimedone (1.05 mmol), 11.3 mg (0.01 mmol) of β-cyclodextrin, stirred at 25°C, reacted for 5 hours, no raw materials were detected by TLC, a large amount of white solid was precipitated in the reaction solution, filtered under reduced pressure to obtain a white powdery solid, ethanol ( 95%, mass percent concentration) recrystallized and vacuum dried to obtain the product 2-amino-3-cyano-4-(4-methylphenyl)-7,7-dimethyl-5-oxo-5,6 ,7,8-tetrahydro-4 H - Benzopyran 290 mg, yield 94%;

[0020] Product structure characterization:

[0021]Melting point: 235°C; IR (KBr) cm -1 : 3383 (NH 2 ), 2968(C-H), 2190(CN), 1690(C=O), 1645(C=C), 1606(C=C); 1 H NMR (500 MHz, DMSO-d6): δ 7.07 (d, 2H, ArH), 7.01-7.00 (d, 2H, ArH), 6.94 (s, 2H, NH 2 ), 4.11 (s, 1H), 2.53 (d, 1H, H-8), 2.48 (d, 1H, H-8′), 2.24-2.21 (d, 1H...

Embodiment 3

[0023] Weigh 140 mg (1.0 mmol) of p-chlorobenzaldehyde into a 25 mL single-necked bottle, add 5 mL of ethanol, stir and mix, then add 79.2 mg (1.2 mmol) of malononitrile and 168 mg of dimedone ( 1.2 mmol), α-cyclodextrin 48.7 mg (0.05 mmol) was stirred at 15°C, reacted for 5 hours, no raw materials were detected by TLC, and a large amount of white solid was precipitated in the reaction solution, which was filtered under reduced pressure to obtain a white powdery solid, ethanol (95 %, mass percent concentration) recrystallized and vacuum dried to obtain the product 2-amino-3-cyano-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7 ,8-tetrahydro-4 H - Benzopyran 294 mg, yield 90%;

[0024] Product structure characterization:

[0025] Melting point: 225°C; IR (KBr) cm -1 : 3448 (NH 2 ), 3040(C-H), 2242(CN), 1600(C=O), 1593(C=C), 1487(C=C); 1 H NMR (500 MHz, DMSO-d 6 ):δ 7.34 (d, J = 8.4 Hz, 2H, ArH), 7.16 (d, J = 8.4 Hz, 2H, ArH), 7.04 (s, 2H, NH 2 ), 4.17 (s, 1H), 2.48 (s, 2H, H...

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Abstract

A preparing method of tetrahydro benzopyran derivatives is disclosed. The method adopts cyclodextrin as a catalyst, adopts aromatic aldehyde, dimedone and malononitrile as raw materials and adopts water, ethanol or methanol as a solvent. A reaction is performed at 15-30 DEG C, and the tetrahydro benzopyran derivatives can be prepared by recrystallization or column chromatography separation after the reaction is finished. The method is mild in reaction conditions, short in process steps, simple and convenient in operation, low in cost and high in yield, and has a good industrial application prospect.

Description

Technical field [0001] The present invention involves a method of preparation of tetrahydrocyrene and pyrarotic, which is specifically 2-amino-3-cyanomyl-4-aromatics-7,7-two-base-5-oxygen-5,6,7,,,,,8-tetrahydrology-4 H -The method of preparation of phenyl pyrarotic series derivatives belongs to the field of organic synthesis. Background technique [0002] Benzene pyraromicid (or tetrahydrocyrene perfurate) compounds have extensive physiological pharmacological activity, such as anti-tumor (TUMOR BIOL., 2014, 35, 5845-5855; bioorg. Med. Chem. Lett., 4458, 4458, 4458-4461.), Antioxidation (med. Chem. Res., 2014, 23, 4907-4914.), Antibacterial (med. Chem. Res., 23, 3569-3584.;2014, 23, 2955-2963.) And Anti-microorganism (Med. Chem. Res., 2013, 22, 3831-3842.). [0003] At present, there have been many methods for synthetic benzene -pyrarotic compounds.For example, Han Guangfan et al. (CN 102424675 B) first produced 2-cyanoparne-3-galcry acrylate under the catalytic catalytic catalys...

Claims

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Application Information

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IPC IPC(8): C07D311/74C07D405/04C07D407/04
CPCC07D311/74C07D405/04C07D407/04
Inventor 廖霞俐张伟任玉峰高凯杨健杨波
Owner KUNMING UNIV OF SCI & TECH
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