80489-00-5

Upstream product

• 109-06-8 α-picoline 
• 2632-10-2 2-bromo-1-(3,4-dichlorophenyl)ethanone 
• 2642-63-9 3',4'-dichloroacetophenone 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 

Downstream Products

• 77823-33-7 (3-Bromo-4-hydroxy-phenyl)-[2-(3,4-dichloro-phenyl)-indolizin-3-yl]-methanone 
• 88273-86-3 Toluene-4-sulfonic acid 2-bromo-4-[2-(3,4-dichloro-phenyl)-indolizine-3-carbonyl]-phenyl ester 
• 77823-66-6 (3,5-Dibromo-4-hydroxy-phenyl)-[2-(3,4-dichloro-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.

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.