A new synthesis method of multi-substituted 4,5,6,7-tetrahydrobenzofuran

A technology of benzofuran and synthesis method, applied in the field of organic chemical synthesis, can solve the problems of residual trace transition metals, low total yield and the like, and achieve the effect of wide applicability of substrates

Active Publication Date: 2022-04-15
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain limitations in the traditional synthesis of 4,5,6,7-tetrahydrobenzofuran: on the one hand, multi-step reactions are often required, the overall yield is low, and the use of transition metals is often involved, resulting in Residual traces of transition metals; on the other hand, there are few general synthesis methods for 4,5,6,7-tetrahydrobenzofuran substituted by the α-position of the 2-position or substituted by the 7-position

Method used

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  • A new synthesis method of multi-substituted 4,5,6,7-tetrahydrobenzofuran
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  • A new synthesis method of multi-substituted 4,5,6,7-tetrahydrobenzofuran

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Experimental program
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Embodiment 1

[0015] Synthesis of 2,3,7-trisubstituted-4,5,6,7-tetrahydrobenzofuran: Add 2-hydroxyl-1, 4-diketone (1,0.2mmol), 1,2-dichloroethane (2.0mL), nucleophile (0.4mmol), 2,2,2-trifluoroacetic acid (0.04mmol), thereafter four Vinyl fluoride plug, the pressure tube was stirred in an oil bath at 80°C for 48 hours, after which the reaction was stopped, the reaction liquid was concentrated, and the product 2 was obtained by column chromatography. Note: When methanol or ethanol is used as the reaction reagent, directly use 2 mL of methanol or ethanol as the reaction solvent without using 1,2-dichloroethane.

[0016] The range of substrates used in this reaction is very wide. Table 1 shows some suitable substrates. Alcohols, amides, furans, indole and other charge-rich substrates can all participate in the reaction. TFA in Table 1 refers to 2,2,2-trifluoroacetic acid, Nucleophiles refers to various types of rich substrates, DCE refers to 1,2-dichloroethane, "or as solvent" means "or use a...

Embodiment 2

[0020] Synthesis of 2,3-disubstituted 4,5,6,7-tetrahydrobenzofuran: Add 2-hydroxy-1,4-di - Ketone (1,0.2mmol), 1,2-dichloroethane (2.0mL), nucleophile (0.4mmol), boron trifluoride ether (0.04mmol). Thereafter, a tetrafluoroethylene stopper was plugged, and the pressure-resistant tube was stirred in an oil bath at 90° C. for 24 hours. Thereafter, the reaction was stopped, the reaction solution was concentrated, and the product 3 was obtained by column chromatography. Note: When methanol or ethanol is used as the reaction reagent, directly use 2 mL of methanol or ethanol as the reaction solvent without using 1,2-dichloroethane.

[0021] The range of substrates used in this reaction is very wide. Table 2 shows some suitable substrates. Alcohols, amides, furans, thiophenes, benzofurans, benzothiophenes, indole and other charge-rich substrates can all participate in the reaction. In Table 2, Nucleophiles refer to various types of electro-rich substrates, DCE refers to 1,2-dichlor...

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Abstract

The invention discloses a new synthesis method of multi-substituted 4,5,6,7-tetrahydrobenzofuran, which uses 2-hydroxyl-1,4-diketone as a starting material, and is catalyzed by an acid to combine with rich electricity Substrates undergo cascade reactions to generate polysubstituted 4,5,6,7-tetrahydrobenzofuran. The charge-rich substrate is one of alcohol, amide, sulfonamide, furan, thiophene, pyrrole, benzofuran, benzothiophene, indole, methoxy substituted benzene and the like. The invention has simple reaction conditions and wide substrate applicability, can be used to synthesize a series of multi-substituted 4,5,6,7-tetrahydrobenzofurans, and is expected to be used in the construction of molecular libraries of related active molecules in the fields of medicine and pesticides. .

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a novel synthesis method of multi-substituted 4,5,6,7-tetrahydrobenzofuran. Background technique [0002] 4,5,6,7-Tetrahydrobenzofuran is a kind of relatively important cyclized skeleton, which has potential application in the field of medicine and pesticide. However, there are certain limitations in the traditional synthesis of 4,5,6,7-tetrahydrobenzofuran: on the one hand, multi-step reactions are often required, the overall yield is low, and the use of transition metals is often involved, resulting in Trace transition metals remain; on the other hand, there are few general synthesis methods for 4,5,6,7-tetrahydrobenzofuran substituted at the α-position of the 2-position or substituted at the 7-position. Contents of the invention [0003] In order to solve the above problems, the present invention provides a new synthesis method of multi-substituted 4,5,6,7-tetrahyd...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/86C07D307/84C07D405/04C07D409/06C07D405/06
CPCC07D307/86C07D307/84C07D405/04C07D409/06C07D405/06
Inventor 沙强刘海璇王俊珂
Owner NANJING AGRICULTURAL UNIVERSITY
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