612065-16-4

Usage

Chemical compound

A substance formed by a chemical reaction or process, with a specific and consistent composition.

Complex and highly specific structure

The compound has a unique arrangement of atoms and bonds that distinguishes it from other chemical compounds.

Hetercyclic compound

Contains one or more rings of atoms, with at least one atom in the ring not being carbon.

Two fused indole rings

The compound has two indole rings that are connected or "fused" together, creating a larger and more complex structure.

Lactam group

A functional group that consists of a carbonyl group (C=O) bonded to a nitrogen atom within a ring.

Pharmacological agent

A substance that has an effect on biological processes and can be used for therapeutic purposes.

Enzyme and receptor inhibition

The compound has shown potential to inhibit certain enzymes and receptors, which are proteins that play a crucial role in various biological processes.

Biological processes

The compound may be involved in or influence various biological processes, such as cell signaling, metabolism, or immune response.

Further research and development

The compound's unique structure and potential medicinal properties make it an interesting candidate for additional study and development in the fields of chemical biology and pharmaceuticals.

InChI:InChI=1/C14H12N2O/c17-14-13-11(8-9-4-3-7-16(9)14)10-5-1-2-6-12(10)15-13/h1-2,5-6,8,15H,3-4,7H2

Upstream product

• 185198-42-9 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester 
• 185198-40-7 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 
• 615-36-1 2-bromoaniline 
• 612065-04-0 trifluoro-methanesulfonic acid 5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl ester 
• 253195-68-5 6-hydroxy-2,3-dihydro-1H-indolizin-5-one 
• 612065-11-9 6-(2-bromo-phenylamino)-2,3-dihydro-1H-indolizin-5-one 

Relevant academic research and scientific papers

1,3-Dipolar cycloaddition chemistry for the preparation of novel indolizinone-based compounds

Starting from methyl 5-oxo-6-trifluoromethanesulfonyloxy-1,2,3,5- tetrahydroindolizine-8-carboxylate, obtained by a Rh(II)-catalyzed 1,3-dipolar cycloaddition reaction of 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one and methyl acrylate, several indolo- and furano-fused indolizinones were efficiently prepared. In the first case, a palladium-mediated C-N coupling of the triflate with a variety of substituted anilines provided the desired methyl 5-oxo-6-(arylamino)-1,2,3,5-tetrahydroindolizine-8-carboxylates in high yield. Methyl 6-(2-bromophenylamino)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate as well as its decarboxylated analogue, 6-(2-bromophenylamino)-2,3-dihydro-1H- indolizin-5-one, were synthesized in excellent yield and were found to undergo an intramolecular Heck cyclization to give 1,2,3,6-tetrahydroindolizino[6,7-b] indol-5-ones. To prepare furano-fused indolizinones, methyl 6-hydroxy-5-oxo-1,2, 3,5-tetrahydroindolizine-8-carboxylate was etherified with different allyl halides, and the resultant allyl ethers were subjected to a thermal Claisen rearrangement to give the corresponding methyl 7-allyl-6-hydroxy-5-oxo-1,2,3,4- tetrahydroindolizine-8-carboxylates. Cyclization under Wacker oxidation conditions afforded methyl 2-methyl-8-oxo-5,6,7,8-tetrahydro-1-oxa-7a-aza-s- indacene-4-carboxylates in near-quantitative yield.

A New β-Carbolinone Synthesis Using a Rh(II)-Promoted [3 + 2]-Cycloaddition and Pd(0) Cross-Coupling/Heck Cyclization Chemistry

(Equation presented) A short and efficient synthesis of the β-carbolinone ring system was achieved using a rhodium(II)-catalyzed [3 + 2]-cycloaddition, a Pd(0)-catalyzed C-N amination reaction, and a subsequent intramolecular Heck reaction as the key synthetic steps.