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2-alkylamino-3-cyanobenzofuran type compound and preparation method thereof

A compound, cyanobenzene technology, applied in the field of 2-alkylamino-3-cyanobenzofuran compounds and preparation, can solve the problems of difficult to scale up production, long reaction time, high price and the like, achieve mild reaction conditions, The effect of short reaction time and simple operation

Active Publication Date: 2015-04-22
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the synthetic methods of reported polyfunctional benzofuran compounds mainly include the following: (1) palladium and copper-catalyzed microwave reaction of o-iodophenol, aromatic terminal alkyne and ethyl iodobenzoate, etc. reaction (Tetrahedron, 2013, 69, 2701-2713), this type of method uses expensive, highly toxic heavy metal catalysts and complex synthons; (2) o-Hydroxybenzaldehyde and α-halogenated amides or α-halogenated ketones The cross-coupling reaction of compounds (Tetrahedron, 2010, 66, 9814-9818), this kind of method requires metal complexes such as chiral Ru or Rh to catalyze, the reaction time is long, and the substrate applicability is narrow; (3) gold-catalyzed 1,3-dicarbonyl compounds and O-aryl hydroxylamine undergo condensation, rearrangement, and cyclization series reactions (J.Org.Chem., 2010, 75, 6300-6303), this method requires expensive gold trichloride Catalyzed with silver hexafluoroantimonate, the cost is high, and the yield of some products is low, so it is difficult to scale up production
At present, there is no report on the preparation of 2-alkylamino-3-cyanobenzofuran compounds using non-aromatic compounds

Method used

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  • 2-alkylamino-3-cyanobenzofuran type compound and preparation method thereof
  • 2-alkylamino-3-cyanobenzofuran type compound and preparation method thereof
  • 2-alkylamino-3-cyanobenzofuran type compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of methyl 2-ethylamino-3-cyanobenzofuran-5-carboxylate

[0029] Add methyl 3-dehydroshikimate (0.19g, 1mmol), malononitrile (0.10g, 1.5mmol) and 10ml of water into the flask, and react in a microwave reactor at 85°C (240W) for 10min. After the completion, the solvent was removed by suction filtration, and the solid obtained above, sodium bicarbonate (0.17g, 2mmol), bromoethane (0.13g, 1.2mmol) and 8ml dimethyl sulfoxide were added to the reaction flask, and heated at 120°C (240W) Microwave reaction for 5 minutes, after the reaction was completed, add 40ml of water, extract with ethyl acetate (3×10ml), combine the extracts, dry over anhydrous magnesium sulfate, concentrate, and separate by column chromatography to obtain 0.20g of light yellow solid, yield 82%, mp 189 -190°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 8.93 (t, J = 5.60Hz, 1H), 7.74 (d, J = 1.60Hz, 1H), 7.71 (dd, J 1 =8.40Hz,J 2 =1.60Hz,1H),7.49(d,J=8.40Hz,1H),3.86(s,3H),3.47(m,2H),1.25(t,J=4.00Hz,3H); ...

Embodiment 2

[0031] Preparation of methyl 2-ethylamino-3-cyanobenzofuran-5-carboxylate

[0032]Add methyl 3-dehydroshikimate (0.19g, 1mmol), malononitrile (0.07g, 1mmol) and 10ml of water into the flask, react in a microwave reactor at 85°C (240W) for 10min, and the reaction is complete Finally, the solvent was removed, and the solid obtained above, sodium bicarbonate (0.17g, 2mmol), bromoethane (0.13g, 1.2mmol) and 8ml dimethyl sulfoxide were added to the reaction flask, and microwaved at 120°C (240W) for 5min After completion of the reaction, add 40ml of water, extract with ethyl acetate (3 × 10ml), combine the extracts, dry over anhydrous magnesium sulfate, concentrate, and separate by column chromatography to obtain 0.16g of light yellow solid, yield 66%, mp 189-190 ℃. The structural analysis data are the same as in Example 1.

Embodiment 3

[0034] Preparation of methyl 2-ethylamino-3-cyanobenzofuran-5-carboxylate

[0035] Add methyl 3-dehydroshikimate (0.19g, 1mmol), malononitrile (0.13g, 2mmol) and 10ml of water into the flask, react in a microwave reactor at 85°C (240W) for 10min, and the reaction is complete Finally, the solvent was removed, and the solid obtained above, sodium bicarbonate (0.17g, 2mmol), bromoethane (0.13g, 1.2mmol) and 8ml dimethyl sulfoxide were added to the reaction flask, and microwaved at 120°C (240W) for 5min After completion of the reaction, add 40ml of water, extract with ethyl acetate (3 × 10ml), combine the extracts, dry over anhydrous magnesium sulfate, concentrate, and separate through column chromatography to obtain 0.20g of light yellow solid, yield 82%, mp 189-190 ℃. The structural analysis data are the same as in Example 1.

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Abstract

The invention belongs to the technical field of chemical synthesis, and discloses a 2-alkylamino-3-cyanobenzofuran type compound and a preparation method thereof. The preparation method of the compound comprises the following steps: (1) dissolving 3-dehydroshikimic acid methyl ester and malononitrile into a solvent A, reacting under a microwave condition, and filtering after the reaction to obtain an intermediate; and (2) performing microwave or oil-bath heating reaction on the intermediate obtained in the step (1) and a bromo-substance in a solvent B under the catalysis of alkali, and separating and purifying a reaction product to obtain the 2-alkylamino-3-cyanobenzofuran type compound. The method for preparing the 2-alkylamino-3-cyanobenzofuran type compound by taking a non-aromatic compound as an initiator is a brand-new method provided by the invention, and has the advantages of simple and easily-available raw material, mild reaction condition, simple operation, short reaction time, high yield and low cost.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a 2-alkylamino-3-cyanobenzofuran compound and a preparation method. Background technique [0002] Multi-substituted benzofurans are a class of heterocyclic compounds with a wide range of biological activities. For example: 2-aryl-5-(3-hydroxy-1-propenyl)-7-ethylbenzofuran compound Ailanthoidol is a natural product extracted from Zanthoxylum bungeanum, which has good antiviral, antifungal and Antioxidant and other activities (Adv.Heterocycl.Chem., 1975,18,337-482); the synthetic 2-alkyl-5-(4-cyanophenyl)benzofuran compound ABT-239 is a kind of H3 receptor Agonist, has anti-Alzheimer's activity (Tetrahedron Lett.,2009,50,7180-7183); and 3-substituted benzoyl-2-butyl-5-methanesulfonamidobenzofuran compound dronedarone Dronedarone has good antiarrhythmic activity and is used as a drug for the treatment of atrial fibrillation and atrial flutter. Due to the go...

Claims

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Application Information

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IPC IPC(8): C07D307/84
CPCC07D307/84
Inventor 王德建邹永张恩生徐田龙魏文
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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