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Synthetic method of 2,4,6-trisubstituted pyridine and fused-ring pyridin-2-one compound
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A technology of ketone compound and synthesis method, which is applied in the field of synthesis, can solve the problems of uncommercialized raw materials, expensive isothiazole catalysts, and inability to purchase, etc., and achieves the advantages of simple operation, simple and easy-to-obtain raw materials and catalysts, and convenient post-treatment Effect
Inactive Publication Date: 2016-06-08
CHINA PHARM UNIV
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However, the synthetic methods reported in the literature have certain limitations.
For example, the AndrewD.Smith group synthesized 2,4,6-trisubstituted pyridines using phenylthioacetic acid as a raw material and isothiazole as a catalyst (Angew.Chem.Int.Ed.2013, 52, 11642-11646), but isothiazole The catalyst is expensive; Chi Yonggui's group used 2-chloroacetate as a raw material and 4-dimethylaminopyridine as a catalyst to synthesize similar 2,4,6-trisubstituted pyridines (Org.Chem.Front.2014, 1, 148-150), but the raw materials are not commercialized and cannot be purchased
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Embodiment 1
[0016] Example 1: 4,6-diphenylpyridin-2-yl-4-methylbenzenesulfonate (I-1)
[0017] Add III-1N-(1,3-diphenylallyl)-4-methylbenzenesulfonamide (108mg, 0.3mmol), bromoacetic acid (50uL, 0.36mmol), 4- Dimethylaminopyridine (44 mg, 0.36 mmol), N,N'-carbonyldiimidazole (58 mg, 0.36 mmol) and diisopropylethylamine (208 uL, 1.5 mmol). After stirring evenly, the temperature was raised to 75°C for 12 hours. The reaction solution was cooled and concentrated, and eluted by column chromatography using a mixed solvent of petroleumether: ethyl acetate with a volume ratio of 10:1 as the eluent to separate and obtain a white powdery solid I-198 mg, with a yield of 82%. MP: 121-123°C.
[0019] Example 2: 4-(4-trifluoromethylphenyl)-6-phenylpyridin-2-yl-4-methylbenzenesulfonate (I-2)
[0020] Using III-2N-[1-phenyl-(3-(4-trifluoromethylphenyl))]allyl-4-methylbenzenesulfonamide (129mg, 0.3mmol) as raw material, the operation method is the same as I -1, to obtain 129 mg of white powdery solid I-2, with a yield of 92%. MP: 163-165°C.
[0022] Example 3: 4-[4-bromophenyl]-6-phenylpyridin-2-yl-4-methylbenzenesulfonate (I-3)
[0023] Using III-3N-[1-phenyl-(3-(4-bromophenyl))]allyl-4-methylbenzenesulfonamide (132mg, 0.3mmol) as raw material, the operation method is the same as I-1, The white powdery solid I-3131mg was obtained, and the yield was 92%. MP: 157-159°C.
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Abstract
The patent relates to the field of organic chemistry, and in particular relates to a synthetic method of 2,4,6-trisubstituted pyridine as shown in a formula I and a fused-ring pyridin-2-one compound as shown in a formula II. The method comprises the following steps of using bromoacetic acid and N-tosyl-1-azadiene as shown in a formula III or 3-substituted vinyl benzosulfamide as shown in a formula IV as raw materials, in the presence of N,N'-carbonyldimidazole, diisopropylethylamine and 4-dimethylamino pyridine, carrying out reactions respectively in a condition of 75 DEG C by using 1,2-dichloroethane as a solvent, cooling and concentrating a reaction liquid, eluting the reaction liquid though column chromatography by using a mixed solvent, in which a volume ratio of petroleumether to ethyl acetate is 10: 1 as an eluting agent, collecting detected eluant parts of all products, and carrying out rotary evaporation on the eluant parts to remove the solvent, so as to obtain the 2,4,6-trisubstituted pyridine and the fused-ring pyridin-2-one compound, which are as shown in the formula I and the formula II. The synthetic method provided by the invention has the advantages that the yield is high, a substrate is wide in applicable aspect, the operation is simple and convenient, the reactions are mild, the after treatment is convenient, the raw materials and a catalyst are simple and obtained easily, and the like.
Description
(1) Technical field [0001] The invention relates to a new method for synthesizing 2,4,6-trisubstituted pyridine and condensed ring pyridin-2 ketone compounds, which belongs to the field of organic chemistry synthesis methodology. (2) Background technology [0002] Pyridine and pyridin-2-one skeletons widely exist in natural products and synthetic drugs with various biological activities. Therefore, the synthesis of pyridine and pyridin-2 ketones has aroused the interest of many chemists. However, the synthesis methods reported in the current literature all have certain limitations. For example, the AndrewD.Smith group synthesized 2,4,6-trisubstituted pyridines using phenylthioacetic acid as a raw material and isothiazole as a catalyst (Angew.Chem.Int.Ed.2013, 52, 11642-11646), but isothiazole The catalyst is expensive; Chi Yonggui's group used 2-chloroacetate as a raw material and 4-dimethylaminopyridine as a catalyst to synthesize similar 2,4,6-trisubstituted pyridines (O...
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