Method for simply and conveniently synthesizing heterocyclic aryl ketone compound

A technology for heterocyclic aryl ketones and compounds is applied in the field of organic synthesis and achieves the effects of low technical difficulty, few experimental steps and easy operation

Inactive Publication Date: 2019-01-04
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some progress has been made in this area, the direct oxidation of C–H bond functionalization using molecular oxygen as a catalyst still faces great challenges.

Method used

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  • Method for simply and conveniently synthesizing heterocyclic aryl ketone compound
  • Method for simply and conveniently synthesizing heterocyclic aryl ketone compound
  • Method for simply and conveniently synthesizing heterocyclic aryl ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-8

[0024] Under an oxygen atmosphere, 0.3 mmol of benzyl heterocycles 1a-1h and 2 mL of dimethyl sulfoxide were sequentially added to a Schlenk reaction tube, heated to 130° C. in an IKA (constant heating magnetic stirrer), and stirred for 48 h. After the reaction was completed, it was cooled to room temperature and quenched with distilled water. It was then extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate. The pure target products 2a-2h were obtained by column chromatography.

Embodiment 1

[0026]

[0027] Under an oxygen atmosphere, 0.3 mmol of 4-benzylpyridine (1a) and 2 mL of dimethyl sulfoxide were sequentially added to a Schlenk reaction tube, heated to 130° C. in an IKA (constant heating magnetic stirrer), and stirred for 48 h. After the reaction was completed, it was cooled to room temperature and quenched with distilled water. It was then extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate. The pure target product 2a (47.8 mg, 87%) was obtained by column chromatography. The characterization data of this compound are as follows: 1 HNMR (600MHz, CDCl 3 ):8.82(d,J=6.0Hz,2H),7.82(dd,J=12.0,6.0Hz,2H),7.65(td,J=9.0,6.0Hz,1H),7.59(dd,J=6.0, 6.0Hz, 2H), 7.52(td, J=9.0, 6.0Hz, 2H); 13 C NMR (101MHz, CDCl 3 ): 195.1, 150.4, 144.3, 135.9, 133.5, 130.1, 128.6, 122.8.

Embodiment 2

[0029]

[0030] Under an oxygen atmosphere, 0.3 mmol 2-benzylpyridine (1b) and 2 mL dimethyl sulfoxide were sequentially added to a Schlenk reaction tube, heated to 140° C. in an IKA (constant heating magnetic stirrer), and stirred for 48 h. After the reaction was completed, it was cooled to room temperature and quenched with distilled water. It was then extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate. The pure target product 2b (42.8 mg, 78%) was obtained by column chromatography. The characterization data of this compound are as follows: 1 HNMR (600MHz, CDCl 3 ): 8.60(dd, J=6.0,6.0Hz,1H),7.96(d,J=12.0Hz,2H),7.91(dd,J=12.0,6.0Hz,1H),7.76(td,J=9.0, 6.0Hz, 1H), 7.47(td, J=9.0, 6.0Hz, 1H), 7.38-7.34(m, 3H); 13 C NMR (101MHz, CDCl 3 ): 193.8, 155.1, 148.5, 137.0, 136.3, 132.9, 131.0, 128.1, 126.2, 124.6.

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Abstract

The invention discloses a method for simply and conveniently synthesizing a heterocyclic aryl ketone compound, and belongs to the technical field of the organic chemistry. The method comprises the following steps: using a benzyl heterocyclic compound as a reaction raw material, in a polar solvent, heating and reacting in an oxygen atmosphere, to obtain a multi-substituted ketone compound. The method is capable of using molecular oxygen as an oxidizing agent, green and environmental, and capable of preparing ketone by directly promoting selective oxidation and functionalization of a Csp3-H bond, and broadening a synthetic method for the ketone compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for conveniently synthesizing heterocyclic aryl ketone compounds. Background technique [0002] As we all know, heterocyclic aryl ketones are an important part of natural products, medicine and pesticides. [0003] Most of the traditional methods to prepare heterocyclic ketones (especially azacyclic ketones) use equivalent toxic and harmful oxidants, and often produce a large number of by-products in the process. Therefore, in the process of synthesizing heterocyclic ketones, using peroxides as oxidants and transition metals as catalysts to oxidize the methylene groups of heterocyclic benzyl groups has been a mature and effective method. [0004] In catalytic chemistry, molecular oxygen is a green and efficient oxidant. Due to its economy and environmental friendliness, the use of molecular oxygen to directly oxidize C-H bonds to carbonyl compound...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07D213/50C07D235/12C07D277/64C07D311/86C07D405/06C07D409/06
CPCC07B41/06C07D213/50C07D235/12C07D277/64C07D311/86C07D405/06C07D409/06
Inventor 刘建明张艳艳岳园园吕庆章王晓培王智贤王科文静
Owner HENAN NORMAL UNIV
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