Synthesis method for 2-arylbenzofuran and derivative thereof
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A derivative, arylbenzene technology, applied in the field of organic synthesis, can solve the problems of expensive catalyst, poor substrate adaptability, difficult raw material preparation, etc. Effect
Inactive Publication Date: 2013-09-04
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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Problems solved by technology
[0006] The above synthetic methods all have technical defects in varying degrees, such as difficult preparation of raw materials, expensive catalysts, poor substrate adaptability, etc.
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Embodiment 1
[0052] This example describes the synthesis test carried out in the reaction system A and in the preferred mode of staged temperature rise.
[0053] The reaction system includes: raw material (1 mmol), inorganic base, copper catalyst, ligand, and reaction medium. Raw material: inorganic base: copper catalyst: ligand: reaction medium=1:3:(0.1~10):0.15:5.
[0054] The raw materials specifically relate to 3-aryl coumarin and its derivatives a1-a10.
[0055] Reaction process: Add the reaction system to the reaction bottle, and add crushed molecular sieves (6 4A molecular sieves) at the same time, connect the drying tube; place the reaction bottle at a temperature of W°C and stir for X hours, then raise the temperature to a temperature of Y°C, and react for Z hours . Keep the system open to the atmosphere during the reaction process.
[0056] Extraction of the crude product: After the reaction, the reaction solution was adjusted to pH=2.0 with hydrochloric acid (6mol / L), extract...
Embodiment 2
[0062] This example describes the synthesis test carried out in the preferred mode of staged temperature rise with the reaction system B.
[0063] The reaction system includes: raw material (1 mmol), copper hydroxide or / and cuprous hydroxide, ligand, and reaction medium. Raw material: copper hydroxide or / and cuprous hydroxide: ligand: reaction medium=1: (2~10): (0.15~10): (5~100).
[0064] Synthesis and product extraction and purification operations are the same as in Example 1.
Embodiment 2
[0065] Table 2 embodiment 2 data records
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Abstract
The invention discloses a synthesis method for 2-arylbenzofuran and a derivative thereof, aims at various degrees of technical defects existing in the conventional synthesis method for 2-arylbenzofuran and the derivative thereof, and provides a method for synthesizing 2-arylbenzofuran and the derivative thereof by taking 3-arylcumarin and a derivative of 3-arylcumarin as the raw materials. The method utilizes carbon-oxygen coupling based on metal catalysis in molecules to achieve synthesis of 2-arylbenzofuran and the derivative thereof by taking 3-arylcumarin and the derivative of 3-arylcumarin as the raw materials. A basic reaction system comprises the raw materials, an alkaline reactant, a copper catalyst, a ligand and a reaction medium, is stirred and heated to a temperature higher than 190 DEG C under an aerobic condition, maintained for 24 hours or more to prepare a reaction liquid, and is subjected to extraction and coarse product purification to prepare a final product. Optimization conditions can adopt two technical means including sectional heating and post-adding of the catalyst. The synthesis method has the advantages that the synthesis raw materials are convenient to obtain, substrate applicability is good, the synthesis technology is simple, the synthesis cost is low, and the synthesis method is particularly suitable for large-scale industrial production.
Description
technical field [0001] The invention relates to a method for synthesizing furan compounds, in particular to a method for synthesizing 2-arylbenzofuran and derivatives thereof, and belongs to the field of organic synthesis. Background technique [0002] 2-Arylbenzofurans are a class of natural organic compounds that widely exist in nature. As a class of heterocyclic compounds with benzofuran skeleton, they have various biological activities, such as anti-tumor, anti-fungal, anti-oxidation, anti-inflammation, anti-platelet aggregation, anti-proliferation, anti-virus, cancer prevention, suppression of immune response, Insecticidal, phytoestrogens and other activities (Wang, Q.A.; Ding, M.; Jing, M., Chin. J. Synth. Chem., 2006, 14, 162.; Von Reuβ, S.H.V.; , W.A., Phytochemistry, 2004, 65, 3113.). Although 2-arylbenzofuran compounds have been found in medicinal plants such as Danshen, Baibu, Jasmine, Zanthoxylum bungeanum, etc., these compounds often coexist with their analog...
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