7496-82-4

Usage

Uses

Used in Organic Synthesis:
2-(4-Methoxy-phenyl)-indolizine is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical entities with potential applications in different industries.
Used in Pharmaceutical Industry:
2-(4-Methoxy-phenyl)-indolizine is used as a building block for the development of new pharmaceuticals. Its specific chemical properties make it a promising candidate for the creation of novel drug molecules with potential therapeutic effects.
Used in Materials Science:
2-(4-Methoxy-phenyl)-indolizine is used as a component in the development of new materials with unique properties. Its incorporation into materials can lead to advancements in areas such as electronics, coatings, and other high-tech applications.
Each of these uses leverages the distinctive attributes of 2-(4-Methoxy-phenyl)-indolizine, highlighting its versatility and the broad scope of its potential impact across scientific and industrial fields.

InChI:InChI=1/C15H13NO/c1-17-15-7-5-12(6-8-15)13-10-14-4-2-3-9-16(14)11-13/h2-11H,1H3

Upstream product

• 109-06-8 α-picoline 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 5469-11-4 p-methoxyphenacyl-α-picolinium iodide 

Downstream Products

• 77823-63-3 (3,5-Dibromo-4-hydroxy-phenyl)-[2-(4-methoxy-phenyl)-indolizin-3-yl]-methanone 
• 7496-41-5 2-(4-hydroxyphenyl)indolizine 
• 96866-66-9 2-(4-methoxyphenyl)octahydroindolizine 
• 1210434-92-6 2-(4-methoxyphenyl)-3-(4,6-dinitro-2,1,3-benzoxadiazol-7-yl)indolizine 
• 1210435-02-1 C₂₁H₁₃N₅O₇ 

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.

Photocatalytic Synthesis of 3-Sulfanyl- and 1,3-Bis(sulfanyl)indolizines Mediated by Visible Light

A metal-free method for the synthesis of 3-sulfanyl indolizines from thiols and 2-arylindolizines, is reported. The reaction is mediated by eosin Y under blue LED light irradiation and uses atmospheric oxygen as oxidant. By the use of a catalytic amount of I2, the corresponding 1,3-bis-sulfanyl indolizines are obtained, in good yields.

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.

Controlling chemoselectivity-application of DMF di-t-butyl acetal in the regioselective synthesis of 3-monosubstituted indolizines

Among a number of DMF dialkyl acetals investigated for the regioselective synthesis of 3-acylindolizines, the di-t-butyl acetal, via its iminium intermediate readily formed in situ, provides the highest chemoselectivity for the intermolecular cyclization of picolinium salts. DMF di-t-butyl acetal was applied to the syntheses of a variety of 3-acylated indolizines including alkyl, aryl, and heteroaryl substituents.

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.