Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes

Abstract

A palladium catalyzed, multicomponent synthesis of indolizines is described via the carbon monoxide driven generation of reactive, pyridine-based 1,3-dipoles.

Synthesis of Propargylamine and Indolazine Derivatives via Three‐Component Reaction Catalyzed by CuOx/CeO2 Materials

“…A common method for the synthesis of indolizines is the cycloaddition of alkenes or alkynes with pyrimidine imines in the presence of a base and oxidizing agent [17] . In recent years, there have been many interesting approaches to synthesize indolizines, such as iodine‐mediated synthesis, metal‐free intramolecular C−N bonding synthesis and transition metal‐catalyzed coupling of multi‐materials containing alkynes, and others [18–22] . The multicomponent coupling reaction is an effective method to obtain many complex structures from simple precursors.…”

“…[17] In recent years, there have been many interesting approaches to synthesize indolizines, such as iodine-mediated synthesis, metal-free intramolecular CÀ N bonding synthesis and transition metal-catalyzed coupling of multi-materials containing alkynes, and others. [18][19][20][21][22] The multicomponent coupling reaction is an effective method to obtain many complex structures from simple precursors. A series of multicomponent syntheses of indolizines consisting of 2-pyridinecarboxaldehyde derivatives, imines and terminal alkynes have been reported under the catalysis of gold, silver, copper or iron.…”

Gold(I)-Catalyzed Functionalization of Pyrrole Derivatives: Stereoselective Synthesis of 7,8-Disubstituted 7,8-Dihydroindolizin-6(5H)-ones

“…Traditionally, the synthesis of indolizines has relied on methods such as the Scholtz and Tschitschibabin reactions (Scheme , eq 1), alongside the classic 1,3-dipolar cycloaddition of pyridinium ylides with electrophilic alkenes or alkynes . Newer methods have recently emerged, utilizing pyrrole units in processes such as annulation, C–H functionalization, or ring-opening reactions .…”

Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

“…Alkynes were widely used as building blocks in the field of organic synthesis and proved to be reliable reaction substrates for the construction of the C−C bond. 8 Therefore, considerable efforts have been made to construct useful frameworks from alkynes. 9 Recently, several important developments have been published, including the alkynylation, alkenylation, and cyclization of alkynes.…”