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Method for synthesizing benzo-oxygen heterocyclic compound

A technology of heterocyclic compounds and synthesis methods, applied in the field of organic chemistry, to achieve the effects of high regioselectivity, strong reaction versatility, and efficient and rapid synthesis

Inactive Publication Date: 2018-11-30
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the deficiencies of the existing synthetic methods, the invention provides a modular synthetic method for benzoxygen heterocyclic compounds with simple operation, high product yield and high regioselectivity

Method used

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  • Method for synthesizing benzo-oxygen heterocyclic compound
  • Method for synthesizing benzo-oxygen heterocyclic compound
  • Method for synthesizing benzo-oxygen heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The reaction formula is as follows:

[0024]

[0025] In a 50mL glass reactor, add 0.5mmol of N-methoxybenzamide, 0.05mmol of palladium acetate catalyst, 1mmol of potassium acetate and 3ml of methylene bromide, and react at 120°C for 36 hours. After treatment, the benzopenta-membered oxygen heterocyclic compound 1a was obtained by silica gel column chromatography as a colorless oily liquid with a yield of 78%. 1H NMR (600MHz, CDCl3): 7.70 (d, J = 7.8Hz, 1H), 7.48 (td, J = 7.8, 1.2Hz, 1H), 7.41 (td, J = 7.8, 0.6Hz, 1H), 7.36 ( dt,J=7.8,1.2Hz,1H),5.45(s,2H),3.96(s,3H).13C NMR(151MHz,CDCl3):157.22,141.31,130.93,128.71,128.23,121.85,121.44,74.70, 62.80.

Embodiment 2

[0027] According to embodiment 1 reaction conditions, only change reaction substrate, obtain product structure and yield as follows:

[0028]

Embodiment 3

[0030] The reaction formula is as follows:

[0031]

[0032] In a 50 mL glass reactor, add 0.5 mmol N-methoxybenzamide, 0.05 mmol palladium acetate catalyst, 1 mmol potassium acetate and 3 mL 1,2-dichloroethane (1,2-DCE) , reacted at 120° C. for 36 hours, after the reaction was finished, the post-treatment was carried out, and the benzo six-membered oxygen heterocyclic compound 2a was obtained by silica gel column chromatography as a light yellow oily liquid with a yield of 75%. 1H NMR (600MHz, CDCl3): 7.89(dd, J=7.8, 0.6Hz, 1H), 7.34(td, J=7.8, 1.8Hz, 1H), 7.29-7.24(m, 1H), 7.20(dd, J =7.8,0.6Hz,1H),4.37(t,J=6Hz,2H),3.95(s,3H),2.98(t,J=6Hz,2H).13C NMR(151MHz,CDCl3):150.73,134.95, 130.09, 127.72, 127.30, 125.50, 125.24, 66.54, 62.70, 28.72.

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Abstract

The invention discloses a method for synthesizing a benzo-oxygen heterocyclic compound and belongs to the technical field of organic synthesis. The method comprises that N-methoxy aryl amide as a reaction raw material and potassium acetate as a base undergo a reaction in dibromomethane or 1, 2-dichloroethane in the presence of palladium acetate as a catalyst under heating conditions to produce thebenzo-oxygen heterocyclic compound. The method is easy to operate, has simple processes, has a wide substrate functional group application range, has good oxygen cyclization and ring reaction zone selectivity and has a high yield.

Description

technical field [0001] The invention relates to carbon-hydrogen bond activation / alkylation catalyzed by a transition metal, in particular to an efficient and convenient synthesis method of a benzoxane heterocyclic compound, belonging to the technical field of organic chemistry. Background technique [0002] Benzooxyheterocyclic compounds are an important class of oxygen-containing heterocyclic compounds, which widely exist in the molecular structures of some natural products. For example, isochromans belong to dihydroisobenzopyran heterocyclic compounds. In the compound structure, the benzo six-membered oxygen heterocycle is its core skeleton, and most of the isochroman compounds have pharmacological activities such as analgesia, antihypertensive, antihistamine and antitumor (Zhang Huaiyuan, Fu Ying. Shandong Chemical Industry, 2013 ,42,4-7). Benzofurans are compounds that widely exist in natural and non-natural products. [0003] 1,3-Dihydroisobenzofuran compounds are imp...

Claims

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Application Information

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IPC IPC(8): C07D307/87C07D307/92C07D311/76
CPCC07D307/87C07D307/92C07D311/76
Inventor 饶伟浩蒋莉莉江欣赵金晓刘晓梦
Owner XINYANG NORMAL UNIVERSITY
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