7496-72-2

Usage

Compound class

Indolizine

Structural characteristic

Bromine atom attached to a phenyl group in the 2-position of the indolizine ring

Potential applications

Organic synthesis, medicinal chemistry, and materials science

Uses

Building block for the synthesis of various organic compounds and pharmaceuticals

Reactivity

Imparted by bromine substituent

Properties

Unique structure and properties that can be utilized in chemical reactions and material design

Versatility

Valuable chemical compound with a range of potential uses and applications

Upstream product

• 82746-41-6 1-(2-(4-bromophenyl)-2-oxoethyl)-2-methylpyridinium bromide 
• 109-06-8 α-picoline 
• 99-73-0 para-bromophenacyl bromide 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 1029804-24-7 2-(4-morpholin-4-ylphenyl)indolizine 
• 1043871-87-9 3-{1-[2-(4-bromophenyl)-indolizin-3-yl]-but-3-enyl}-1H-indole 
• 1187471-79-9 4-[2-(4-bromophenyl)indolizin-3-yl]-2-chloroquinazoline 
• 79283-31-1 [2-(4-Bromo-phenyl)-indolizin-3-yl]-[3,5-dichloro-4-(3-dibutylamino-propoxy)-phenyl]-methanone; compound with oxalic acid 
• 79283-29-7 [2-(4-Bromo-phenyl)-indolizin-3-yl]-[3,5-dichloro-4-(3-dipropylamino-propoxy)-phenyl]-methanone; compound with oxalic acid 
• 79286-15-0 [2-(4-Bromo-phenyl)-indolizin-3-yl]-[3-chloro-4-(3-dibutylamino-propoxy)-phenyl]-methanone; compound with oxalic acid 
• 79285-91-9 [3-Bromo-4-(3-dibutylamino-propoxy)-phenyl]-[2-(4-bromo-phenyl)-indolizin-3-yl]-methanone; compound with oxalic acid 
• 79286-14-9 [2-(4-Bromo-phenyl)-indolizin-3-yl]-[3-chloro-4-(3-dipropylamino-propoxy)-phenyl]-methanone; compound with oxalic acid 
• 77823-31-5 (3-Bromo-4-hydroxy-phenyl)-[2-(4-bromo-phenyl)-indolizin-3-yl]-methanone 

Relevant academic research and scientific papers

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.

Regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions

An efficient and straightforward metal-free regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide has been described. A series of indolizine-dithiocarbamate derivatives were easily accessed in moderate to good yields with a broad scope. In addition, imidazo[1,2-a]pyridines were also well tolerated to afford diverse imidazoheterocycle-dithiocarbamate products, which are expected to be utilized for drug discovery. Of note, the reaction could be readily scaled up, and shows its practical value in organic synthesis.

Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials

A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.

Visible-Light-Induced Regioselective Dicarbonylation of Indolizines with Oxoaldehydes via Direct C-H Functionalization

A metal-free system for regioselective dehydrogenative cross-couplings between indolizines and oxoaldehydes catalyzed by visible light under mild conditions has been described. As an atom economical and eco-friendly protocol, the reaction proceeds in good yields using inexpensive, readily available visible-light sources and the environmentally friendly oxidant oxygen. Various valuable 1,2-dicarbonyl derivatives attached to an indolizine core were easily accessed by the direct dicarbonylation of the sp2 C-H bond.

NH4I-catalyzed C–S bond formation via an oxidation relay strategy: Efficient access to dithioether decorated indolizines

An efficient NH4I-catalyzed C–H/S–H cross-coupling reaction of indolizines with thiols is reported. Compared to previous methods, this environmentally friendly oxidation relay strategy uses O2 as an oxidant to afford dithioether decorated indolizines in up to 98% yield. Promising results have been obtained, indicating the high applicability and atom economy of this method.

A visible-light-induced intermolecular [3 + 2] alkenylation-cyclization strategy: Metal-free construction of pyrrolo[2,1,5-cd] indolizine rings

A simple and efficient visible-light-induced intermolecular [3 + 2] alkenylation-cyclization process has been developed. This reaction provided an unprecedented metal-free double C(sp2)-H bond oxidation coupling of indolizines with electron-deficient alkenes. Through this cascade reaction, a series of pyrrolo[2,1,5-cd]indolizine derivatives with a large π-system were synthesized. Furthermore, this approach features easily available starting materials, good functional group tolerance, step-economy, high efficiency and mild conditions.

Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines

An efficient transition-metal-free regioselective C-H/S-H cross-coupling of indolizines with thiols has been developed for the first time to describe a workable route to indolizine thioethers. This finding provides a new method and more straightforward pathway for controllable synthesis of mono- or dithiolation indolizines that are otherwise difficult to obtain by the literature methods. The reaction exhibits good functional group tolerance and high efficiency and affords the products in good to excellent yields.

Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines

A variety of novel 2,5-diaryl-indolizines have been prepared through the palladium-catalyzed cross-coupling reactions of organozinc reagents prepared from 2-aryl-indolizines with aromatic halides. The photophysical properties of representative compounds indicate that the 2,5-diaryl-indolizines are promising candidates to be used in optoelectronic devices and biomolecular labeling. In addition, cyclic voltammetry studies of some nitrophenyl-substituted indolizines have shown evidences of an oxidation process without the correspondent reduction peak suggesting a dimerization reaction.

A Practical Parallel Synthesis of 2-Substituted Indolizines

A practical parallel synthesis of 2-substituted indolizines 4 via phase-separation techniques is reported. Their further transformation into indolizidines 5 is also described.