16806-93-2

Usage

Uses

Used in Pharmaceutical Industry:
6,7-Dihydro-4(5H)-benzofuranone is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those containing the furacridone ring skeleton. Its unique structure and properties make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 6,7-Dihydro-4(5H)-benzofuranone serves as a versatile intermediate for the synthesis of a wide range of organic compounds. Its ability to participate in various chemical reactions, such as electrophilic aromatic substitution and nucleophilic addition, makes it a useful component in the creation of complex organic molecules for research and industrial applications.

Synthesis Reference(s)

Tetrahedron, 51, p. 3087, 1995 DOI: 10.1016/0040-4020(95)00070-OTetrahedron Letters, 27, p. 1127, 1986 DOI: 10.1016/S0040-4039(00)84195-7

InChI:InChI=1/C8H8O2/c9-7-2-1-3-8-6(7)4-5-10-8/h4-5H,1-3H2

Upstream product

• 35768-38-8 3-hydroxy-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 107-20-0 2-chloroethanal 
• 504-02-9 1,3-cylohexanedione 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 66144-45-4 4-Furan-2-yl-butyryl chloride 
• 30182-67-3 1,3-Cyclohexanedione 
• 183495-78-5 2-phenylsulfanyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 150-78-7 1,4-dimethoxybezene 
• 119-61-9 benzophenone 
• 84099-58-1 4-hydroxy-4,5,6,7-tetrahydrobenzofuran 
• 1460-08-8 2-diazocyclohexane-1,3-dione 
• 75-35-4 1,1-Dichloroethylene 
• 108-05-4 vinyl acetate 

Downstream Products

• 51471-08-0 1-methyl-1,5,6,7-tetrahydro-indol-4-one 
• 13671-74-4 1-benzyl-4-oxo-4,5,6,7-tetrahydroindole 
• 480-97-7 4-hydroxybenzofuran 
• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 84099-58-1 4-hydroxy-4,5,6,7-tetrahydrobenzofuran 
• 42768-88-7 4,5,6,7-tetrahydro-4-benzofuran 
• 61190-46-3 6,7-dihydro-1-benzofuran-4(5H)-one oxime 
• 180339-33-7 4,5,6,7-tetrahydrobenzo[b]furan-4-one (Z)-oxime 
• 180339-32-6 4,5,6,7-tetrahydrobenzo[b]furan-4-one (E)-oxime 
• 219989-24-9 5,6,7,8-tetrahydrofuro[3,2-b]azepine 

Relevant academic research and scientific papers

A concise new synthesis of angular furanocoumarins: Angelicin, oroselone and oroselol

An efficient synthesis of angular furanocoumarins has been carried out starting from dihydrobenzofuran derivatives.

CYCLIZATIONS OF SOME FURYL ACID CHLORIDES

Intramolecular Friedel-Crafts acylation of the furan ring has been accomplished in good yields with stannic chloride for both furyl isomers of butyryl acid chloride.The propionyl chloride isomers, however, failed to produce reasonable quantities of the cyclic ketone.

Preparation method of polysubstituted furan compound

The invention discloses a preparation method of a polysubstituted furan compound, which comprises the following steps: by using a carbonyl compound with an electron withdrawing group at the alpha position and dichloroolefin as raw materials, reacting under alkaline conditions to obtain a 2, 3-disubstituted furan compound and a 2, 3, 5-trisubstituted furan compound. The method has the advantages ofno need of transition metal catalysis, strong substrate applicability, cheap and easily available raw materials, simple operation, high efficiency and wide application prospect.

ANTIMICROBIAL AGENTS AND COMPOSITIONS AND USES THEREOF

Described herein are compounds that act as antimicrobial agents, compositions comprising these compounds, and methods of their use in to treating infections caused by Helicobacter pylori (H. pylori) or killing or inhibititing the growth of H. pylori.

Transition-Metal-Free Approach to Polysubstituted Furans

A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance.

CXCR2 ANTAGONIST

A compound as a CXCR2 antagonist and an application thereof in preparing a drug as a CXCR2 antagonist. In particular, the present invention relates to a compound represented by formula (II) or an isomer or pharmaceutically acceptable salt thereof.

Preparation method and application of pongamol

The invention belongs to the field of medicinal chemistry, and relates to a preparation method and application of pongamol. The preparation method comprises the following steps: with 1,3-cyclohexanedione (6) as a starting raw material, carrying out a cyclization reaction to obtain 6,7-dihydro-4-(5H)-benzofuranone (7); carrying out acylation reaction on the compound (7) to obtain 5-acetyl-6,7-dihydro-4-(5H)-benzofuranone (8); carrying out dehydrogenation reaction on the compound (8) to obtain 1-(4-hydroxy-5-benzofuryl) ethyl ketone (3); carrying out methylation reaction on the compound (3) to obtain 1-(4-methoxy-5-benzofuryl) ethyl ketone (4); and condensing the compound (4) with benzoyl chloride to obtain the pongamol. According to the preparation method, the selected reagents are cheap and easy to obtain, the post-treatment method is simple, the reaction conditions are mild, and the product yield is high. Pharmacological activity experiments show that the synthesized compound has nerve injury resistance and anti-inflammatory activity, which means that the compound has a good application prospect in the field of treatment of nerve injury and inflammation related diseases.

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

AgBF4/[Bmim]BF4-Catalyzed [3+2] cycloaddition of cyclic diazodicarbonyl compounds: Efficient synthesis of 2,3-dihydrofurans and conversion to 3-acylfurans

A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF4

Investigation of furo[2,3-h]- and pyridazino[3,4-f]cinnolin-3-ol scaffolds as substrates for the development of novel HIV-1 integrase inhibitors

With the aim to develop novel HIV-1 integrase inhibitors, we obtained a set of condensed ring systems based on the furo[2,3-h]cinnolin-3(2H)-one and pyridazino[3,4-f]cinnolin-3-ol scaffolds bearing a potential chelating pharmacophore, which can be involved in the inhibition mechanism of the enzyme. Herein, we report the design, synthesis, structural investigation and preliminary biological results of these heteroaromatic systems. ARKAT-USA, Inc.