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Preparation method of tetrahydropyranoisoindole compounds

A technology of tetrahydropyran and isoindole, which is applied in the field of preparation of tetrahydropyranoisoindole compounds, can solve the problems of metal catalysis, cumbersome operation, harsh reaction conditions, etc., and achieve easy availability of raw materials and easy operation Simple, scientific and reasonable synthesis method

Active Publication Date: 2020-03-24
上海鲲博玖瑞医药科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Synthesis of tetrahydropyranoisoindole compounds using the above method has certain shortcomings and deficiencies: 1) metal catalysis is required; 2) complex operations; 3) harsh reaction conditions

Method used

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  • Preparation method of tetrahydropyranoisoindole compounds
  • Preparation method of tetrahydropyranoisoindole compounds
  • Preparation method of tetrahydropyranoisoindole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of tetrahydropyranoisoindole compound 2a

[0025]

[0026] N-methoxy-3-((3-phenylprop-2-yn-1-yl)oxy)benzamide (0.2mmol, 56mg), bistrifluoromethanesulfonimide (0.04mmol, 11 mg), add 4.0 mL of DCE (dichloroethane) into a 15 mL thick-walled pressure-resistant tube, and stir at 100°C for 12 hours. After the reaction was completed, 4-methoxytetrahydropyranoisoindole 3a (0.16 mmol, 45 mg) was obtained by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), Isolated yield 80%.

[0027] Spectral analysis data 2a:

[0028] 1 H NMR (500MHz, CDCl 3 ): δ7.54–7.45(m,2H),7.39–7.31(m,3H),7.21–7.13(m,2H),7.09(dd,J=5.4,3.4Hz,1H),4.62–4.44(m ,1H),4.07–3.99(m,1H),3.99(s,3H),3.15–2.98(m,1H),2.21(td,J=13.3,4.7Hz,1H). 13 C NMR (125MHz, CDCl 3 ): δ166.9, 152.1, 137.9, 131.2, 129.8, 128.7, 128.6, 128.1, 127.5, 118.9, 115.8, 65.2, 64.7, 64.0, 31.7.

Embodiment 2

[0030] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0031]

[0032] Spectrum analysis data 2b:

[0033] 1 H NMR (500MHz, CDCl 3 ):δ7.43(q,J=4.1,3.4Hz,2H),7.08–6.99(m,3H),6.81(d,J=8.8Hz,2H),4.53–4.40(m,1H),4.03– 3.95(m,1H),3.92(s,3H),3.76(s,3H),2.96(d,J=12.8Hz,1H),2.13(td,J=13.2,4.7Hz,1H). 13 C NMR (125MHz, CDCl 3 ): δ167.0, 159.7, 152.1, 131.2, 130.1, 129.8, 128.8, 128.4, 119.0, 115.8, 114.0, 65.3, 64.70, 63.8, 55.3, 32.0.

Embodiment 3

[0035] Replace 1a in Example 1 with 1c, other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0036]

[0037] Spectrum analysis data 2c:

[0038] 1 H NMR (500MHz, CDCl 3 ):δ7.46–7.43(m,2H),7.12(d,J=8.1Hz,2H),7.06–6.99(m,3H),4.55–4.41(m,1H),4.04–3.97(m,1H ),3.94(s,3H),3.01(d,J=12.9Hz,1H),2.32(s,3H),2.15(td,J=13.3,4.7Hz,1H). 13 C NMR (125MHz, CDCl 3 ): δ167.0, 152.1, 138.5, 135.0, 131.2, 129.8, 129.4, 128.4, 127.4, 118.9, 115.8, 65.3, 64.7, 63.9, 31.7, 21.1.

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Abstract

The invention discloses a preparation method of tetrahydropyranoisoindole compounds, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding N-methoxy-3-((3-phenylpropyl-2-alkyn-1-yl)oxy)benzamide (0.2 mmol, 56mg), bis(trifluoromethanesulfonyl)imide (0.04 mmol, 11 mg) and 4.0 mL of DCE (dichloroethane) into a 15 mL thick walled pressure-resistant tube, and performing stirring at 100 DEG C for 12 h; and carrying out chromatographic separation by using a silica gel column after the reaction is finished in order to obtain the pure target products.The preparation method of the tetrahydropyranoisoindole compounds has the characteristics of scientificity, reasonability, simplicity in operation and the like. The reaction equation of the method isshown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of tetrahydropyranoisoindole compounds. Background technique [0002] Tetrahydropyranoisoindole derivatives have important application value in organic synthesis and medicinal chemistry. They have a wide range of pharmacological activities, such as the treatment of nerve and cardiovascular tissue damage. In this class of molecules, tetrahydropyranoisoindole has been shown to be effective antipsychotic (Crystallogr.Spectrosc.Res.1991,21,431), anti-infective (Bioorg.Med.Chem.Lett.2006,16,4031 ) and immune agents (Mini-Reviews in Medicinal Chemistry.2007, 7,707). [0003] In view of the wide range of biological activities and application value of tetrahydropyranoisoindole compounds, it is of great significance to develop a new method for the practical and effective synthesis of tetrahydropyranoisoindole compounds. [0004] The preparatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/06
CPCC07D491/06
Inventor 张林宝孙绳政李明文丽荣
Owner 上海鲲博玖瑞医药科技发展有限公司