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Synthesis method of carbonyl-substituted benzodihydrofuran and benzodihydropyran compound

A technology for chroman compounds and chroman, which is applied in the field of synthesis of carbonyl-substituted chroman and carbonyl-substituted chroman compounds, can solve the problem of long reaction time and unexplored bottom-line problems. Problems such as general applicability and low yield

Pending Publication Date: 2021-11-30
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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Problems solved by technology

However, these synthetic methods have limitations such as low yield, long reaction time, and lack of substrate universality. The specific limitations are shown in Table 1.
[0003] Table 1 The limitations of the reported synthesis methods of carbonyl-substituted chroman and chroman compounds

Method used

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  • Synthesis method of carbonyl-substituted benzodihydrofuran and benzodihydropyran compound
  • Synthesis method of carbonyl-substituted benzodihydrofuran and benzodihydropyran compound
  • Synthesis method of carbonyl-substituted benzodihydrofuran and benzodihydropyran compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: A kind of synthetic method of carbonyl substituted chroman compound:

[0029] Add 1mmol of PPA and 0.3mL of solvent DMF into a 5mL pressure-resistant reaction bottle, then add 0.2mmol of raw material I1, stir and react in an oil bath at 130°C for 10h; after the reaction, extract with ethyl acetate three times, wash with water and saturated sodium chloride solution in turn The organic layer was dried and washed with anhydrous sodium sulfate, filtered, and the residue after the filtrate was concentrated under reduced pressure was subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =5:1) Separation and purification to obtain carbonyl-substituted chroman dihydrofuran compound II1 with a yield of 81%.

[0030] The NMR of the prepared carbonyl-substituted chroman compound (II1) ( 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, CDCl 3 )δ10.23(s, 1H), 7.59(d, J=7.8Hz, 1H), 7.38(dd, J=7.2, 1.2Hz, 1H), 6.92(t, J=7.5Hz, 1H), 5.12( ddq,J=12.7...

Embodiment 2

[0031] Embodiment 2: A kind of synthetic method of carbonyl substituted chroman compound:

[0032] Add 1mmol of PPA and 0.3mL of solvent DMF into a 5mL pressure-resistant reaction bottle, then add 0.2mmol of raw material Ⅰ2, stir and react in an oil bath at 150°C for 6h; after the reaction, extract with ethyl acetate three times, wash with water and saturated sodium chloride solution in turn The organic layer was dried and washed with anhydrous sodium sulfate, filtered, and the residue after the filtrate was concentrated under reduced pressure was subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =5:1) separation and purification to obtain carbonyl-substituted chroman dihydrofuran compound II2 with a yield of 52%.

[0033] The NMR of the prepared carbonyl substituted chroman compound (Ⅱ2) ( 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, CDCl 3 )δ9.82(s,1H),7.36(s,1H),7.34(s,1H),5.19–5.12(m,1H),3.96(s,3H),3.43(dd,J=15.4,9.0Hz ,1H),2.93(dd,J=15.4,7.8...

Embodiment 3

[0034] Embodiment 3: A kind of synthetic method of carbonyl substituted chroman compound:

[0035] Add 4mmol of PPA, 0.3mL of solvent DMF and 0.2mmol of raw material Ⅰ3 into a 5mL pressure-resistant reaction bottle, stir and react in an oil bath at 90°C for 10h; after the reaction, extract with ethyl acetate three times, and wash the organic layer with water and saturated sodium chloride solution in sequence , then dry the washed organic layer with anhydrous sodium sulfate, filter, and the residue after the filtrate is concentrated under reduced pressure is subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =4:1) separation and purification to obtain carbonyl-substituted chroman dihydrofuran compound II3 with a yield of 78%.

[0036] The NMR of the prepared carbonyl substituted chroman compound (Ⅱ3) ( 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, CDCl 3 )δ7.84(s,1H),7.82(d,J=8.4,1.8Hz,1H),6.79(d,J=8.4Hz,1H),5.05(m,J=8.8,7.3,6.4Hz,1H ),3.38(dd,J=15....

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Abstract

The invention provides a synthesis method of carbonyl-substituted benzodihydrofuran and a carbonyl-substituted benzodihydropyran compound, the method specifically comprises the following steps: adding polyphosphoric acid PPA, a solvent N, N-dimethylformamide DMF and carbonyl-substituted o-allyl / carbonyl-substituted isopentenyl phenol into a pressure-resistant reaction flask, and heating and stirring to react for 2-10 hours; and after the reaction is finished, separating and purifying to obtain the carbonyl-substituted benzodihydrofuran / carbonyl-substituted benzodihydropyran compound. The synthesis method is disclosed for the first time, the reaction time is short, the catalyst PPA is low in price and easy to obtain, the substrate is good in universality, the product yield is good, a new method is provided for synthesis of the carbonyl-substituted benzodihydrofuran and the carbonyl-substituted benzodihydropyran compound, and a foundation is laid for large-scale production of products and improvement of production efficiency.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a synthesis method of carbonyl-substituted chroman and carbonyl-substituted chroman. Background technique [0002] Chromene and chroman systems exist in a large number of biologically active compounds, and have significant biological activities, such as anti-genotoxicity, anti-proliferation, anti-cancer and anti-inflammation, etc. The reported preparation of benzodihydrofuran The most common method for hydrofuran and chroman compounds is the intramolecular cyclization of o-allyl / prenylphenol. Carbonyl-substituted chroman and chroman compounds also have a wide range of biological activities, such as anti-cancer, anti-proliferation and inhibitory activity on D-amino acid oxidase. Carbonyl substituted chroman, chroman compound synthetic method mainly is to use I 2 (Heterocycles.1995,41:219-223), H 2 SO 4 (Lett Org Chem.2009,6:29-36; Synthesis.2010,21:3745-3754; Eur J ...

Claims

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Application Information

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IPC IPC(8): C07D307/79C07D311/58C07D493/04C07D493/14
CPCC07D307/79C07D311/58C07D493/04C07D493/14
Inventor 杨礼寿杨小生王恩花杨倩彭梅李齐激王瑜罗忠圣李良群邓廷飞曹家辅葛丽娟李立朗
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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