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Method for synthesizing benzo-oxygen heterocyclic compound
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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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[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
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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 methylenebromide, and react at 120°C for 36 hours. After treatment, the benzopenta-membered oxygen heterocyclic compound 1a was obtained by silica gelcolumn 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 gelcolumn 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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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...
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