50640-00-1

Usage

Structure

A derivative of indole with a tetrahydrofuran group attached to the indole ring

Classification

Heterocyclic compound

Natural occurrence

Commonly found in natural products and pharmaceuticals

Chemical properties

Unique due to the presence of the tetrahydrofuran group

Potential applications

Drug discovery and synthesis

Biological activity

Studied for its potential as an anti-inflammatory and anticancer agent

Use in organic chemistry

Acts as a building block for the synthesis of more complex molecules with potential therapeutic benefits

Versatility

Has potential applications in both medicinal and synthetic chemistry

Upstream product

• 50639-98-0 3-(2-tetrahydrofuranylthio)-indole 
• 109-99-9 tetrahydrofuran 
• 120-72-9 indole 
• 651712-31-1 4-hydroxy-1-(indol-1-yl)butane-1-thione 

Relevant academic research and scientific papers

Copper-Catalyzed Oxidative Dehydrogenative C(sp3)?H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources

A copper-catalyzed oxidative C(sp3)?H/N?H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)?N bond formation through a radical pathway generated by homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerates a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl, and methoxy. free-NH-containing indoles, pyrroles, pyrazoles, indazoles, and benzotriazoles are successfully N-alkylated.

Transition metal-free intermolecular a-C-H amination of ethers at room temperature

We describe a new method for the intermolecular amination of the α-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.

Synthesis of N-Glycoside Analogs via Thionolactones

Indolyl N-glycoside analogs were obtained by a two-step sequence via indole N-thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N-thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N- over C3-acylation. Treatment of the ω-hydroxy-thioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N-(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the ω-hydroxyl group can give access to tetrahydrothiophene N-glycosides.