Dihydrofuran heterocyclic compounds and synthesis process thereof

Abstract

A dihydrofuran compound is prepared through the reaction of the electron-deficiency diene and alkyne with the nucleophilic reagent with dual nucleophilic sites. Its advantages are simple preparing process and high yield.

Description

technical field

[0001] The invention relates to a heterocyclic compound and a synthesis method thereof, in particular to a dihydrofuran compound and a synthesis method thereof. Background technique

[0002] Dihydrofuran organic heterocyclic compounds are widely used in organic synthesis, pesticides, medicine and other fields, and are important structural units of chemical products in these fields. These structural units are also included in many molecules with physiological activity. For example, Compound 1 is an enzyme inhibitor (Lee, D.-S.; Lee, S.-H.; Nah, J.-G; Hong, S.-D. Biosci. Biotechnol. Biochem. 1999, 63 , 2236), Compound 2 is an ion channel blocker involved in immune function (Butenschn, I; Mller K.; Hnsel, W.J.Med.Chem.2001, 44, 1249). Compound 3 is a substance with anti-platelet aggregation effect isolated from natural products (Jong, T.T.; Wu, T.S. Phytochemistry(s) 1989, 28, 245). Compound 4 is a natural product with anthelmintic effect (Kato, S.; Shibay...

Examples

Embodiment 1

[0020] The following examples will help to understand the present invention, but do not limit the content of the present invention. Example 1: Reaction of an electron-poor allene with a carbon-oxygen double-center nucleophile in the presence of triphenylphosphine.

[0021] In toluene, add triphenylphosphine (0.2mmol) and corresponding carbon-oxygen double-center nucleophile (1mmol), heat up to 70-80°C to dissolve, then add electron-poor allene (1mmol) in toluene solution ( In the synthesis reaction of compound P2, P3, P4, P5, the toluene solution of electron-poor allene is slowly added dropwise to the reaction system with a syringe pump), and the reaction is continued until thin layer chromatography shows that the raw material disappears, the solvent is removed under reduced pressure, and the column Chromatography gave the corresponding dihydrofuran derivative. P1: (Reactants: ethyl 2,3-butadienoate, cyclohexanedione) IR (neat) ν2947, 1736, 1635, 1404, 1181cm -1 . 1 H NMR...

technical field

[0001] The invention relates to a heterocyclic compound and a synthesis method thereof, in particular to a dihydrofuran compound and a synthesis method thereof. Background technique

[0002] Dihydrofuran organic heterocyclic compounds are widely used in organic synthesis, pesticides, medicine and other fields, and are important structural units of chemical products in these fields. These structural units are also included in many molecules with physiological activity. For example, Compound 1 is an enzyme inhibitor (Lee, D.-S.; Lee, S.-H.; Nah, J.-G; Hong, S.-D. Biosci. Biotechnol. Biochem. 1999, 63 , 2236), Compound 2 is an ion channel blocker involved in immune function (Butenschn, I; Mller K.; Hnsel, W.J.Med.Chem.2001, 44, 1249). Compound 3 is a substance with anti-platelet aggregation effect isolated from natural products (Jong, T.T.; Wu, T.S. Phytochemistry(s) 1989, 28, 245). Compound 4 is a natural product with anthelmintic effect (Kato, S.; Shibay...

Examples

Embodiment 1

[0020] The following examples will help to understand the present invention, but do not limit the content of the present invention. Example 1: Reaction of an electron-poor allene with a carbon-oxygen double-center nucleophile in the presence of triphenylphosphine.

[0021] In toluene, add triphenylphosphine (0.2mmol) and corresponding carbon-oxygen double-center nucleophile (1mmol), heat up to 70-80°C to dissolve, then add electron-poor allene (1mmol) in toluene solution ( In the synthesis reaction of compound P2, P3, P4, P5, the toluene solution of electron-poor allene is slowly added dropwise to the reaction system with a syringe pump), and the reaction is continued until thin layer chromatography shows that the raw material disappears, the solvent is removed under reduced pressure, and the column Chromatography gave the corresponding dihydrofuran derivative. P1: (Reactants: ethyl 2,3-butadienoate, cyclohexanedione) IR (neat) ν2947, 1736, 1635, 1404, 1181cm -1 . 1 H NMR...

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