A method for synthesizing pyrrolo[3,4-c]pyrazole-4,6(1h,5h)dione derivatives

A 4-c and derivative technology, applied in the direction of organic chemistry, can solve the problems of low conversion rate and yield, unfavorable industrialization, and many side reactions, and achieve high conversion rate and yield, good applicability, and side reactions little effect

Active Publication Date: 2022-04-29
CHENGDU CHEMPARTNER
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The technical problem to be solved by this invention is that in the prior art, 3-bromo-1-methyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives There are many steps in the synthetic method, many side reactions, low conversion rate and yield, no shared intermediates to simplify the synthesis, poor applicability, expensive reagents, high cost, and unfavorable defects such as industrialization

Method used

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  • A method for synthesizing pyrrolo[3,4-c]pyrazole-4,6(1h,5h)dione derivatives
  • A method for synthesizing pyrrolo[3,4-c]pyrazole-4,6(1h,5h)dione derivatives
  • A method for synthesizing pyrrolo[3,4-c]pyrazole-4,6(1h,5h)dione derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1, Synthesis of 3-bromo-1-methyl-5-phenylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione (Formula A-a)

[0067]

[0068] Step 1. Add an aqueous solution of sodium formate (4.4g sodium formate dissolved in 25mL of purified water) to the ethanol (25mL) solution of raw material compound A-1 (1.0g), then drop the temperature in an ice bath to 0°C and add bromine (4.8g ), the reaction solution was stirred for 3 hours; after the reaction was completed, the reaction system was added with water (30mL) to extract it and extracted with ethyl acetate, the organic phase was collected and washed with saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to remove the solvent, and the residue Separation and purification by column chromatography gave compound A-2 (1.2 g, yield 81%) as a yellow solid;

[0069] Step 2. Add toluene (20mL) solvent to aniline (compound A-3a) (0.9g), cool down to 0°C in an ice bath, add 2N trimethylaluminum toluene...

Embodiment 2

[0074] Example 2, 3-bromo-5-(3-chloro-4-fluorophenyl)-1-methylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione (formula Synthesis of A-b)

[0075]

[0076] Step 1. Add the aqueous solution of sodium acetate (4g sodium acetate dissolved in 35mL pure water) to the ethanol (25mL) solution of raw material compound A-1 (1.0g), then cool down to 0°C in an ice bath and add bromine (4g ), the reaction solution was stirred for 5 hours; after the reaction was completed, the reaction system was added with water (30mL) to extract it and extracted with ethyl acetate, the organic phase was collected and washed with saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to remove the solvent, and the residue Separation and purification by column chromatography gave compound A-2 (1.3 g, yield 85%) as a yellow solid;

[0077] Step 2. Add benzene (29mL) solvent to 3-chloro-4-fluoroaniline (compound A-3b) (1.2g), cool to 0°C in an ice bath and add 2N trimethylal...

Embodiment 3

[0082] Example 3, Synthesis of 3-bromo-5-(4-methylphenyl)-1-methylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione (Formula A-c)

[0083]

[0084] Synthesized by an operation similar to that of Example 1 to obtain the target product compound 3-bromo-5-(4-methylphenyl)-1-methylpyrrole[3,4-c]pyrazole-4,6(1H, 5H) - diketones (formulas A-c).

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Abstract

The invention provides a new method for synthesizing 3-bromo-1-methyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives. 3-bromo-1-methyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione Derivatives; the synthetic method of the present invention has short steps in the entire synthetic route, few side reactions, high conversion rate and yield, simplified method for shared intermediates, wide application of substrates, mild operating conditions, high safety, and is conducive to scale-up production and Industrialization promotion and application.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, and more specifically, relates to a new method for synthesizing pyrrolo[3,4-c]pyrazole-4,6(1H,5H)dione derivatives. Background technique [0002] 3-Bromo-1-methyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives are an important class of intermediate compounds with the structure of formula A Shown: [0003] [0004] At present, the synthesis method of 3-bromo-1-alkyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives disclosed in the prior art literature is to use aromatic Amines are used as starting materials to synthesize pyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives with ring-closing structures, followed by a series of functional group conversion reactions to finally obtain the product compound 3-Bromo-1-alkyl-5-arylpyrrole[3,4-c]pyrazole-4,6(1H,5H)-dione derivatives, the route is as follows: [0005] [0006] There are many defects in the abov...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 仵清春鲍龙
Owner CHENGDU CHEMPARTNER
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