FeCl3-catalyzed formation of indolizine derivatives via the 1,3-dipolar cycloaddition reaction between azomethine ylides and chalcones or dibenzylideneacetones

CuBr-Catalyzed Aerobic Decarboxylative Cycloaddition for the Synthesis of Indolizines under Solvent-Free Conditions

“…Pyridine annulation is an important strategy for indolizine synthesis and is mainly accomplished by four routes (part A of Scheme ): 1,3-dipolar cycloaddition of activated alkynes or alkenes with pyridinium salts derived from pyridines and organic halides; intramolecular or intermolecular cyclization of C2-substituted pyridines; , transannulation reaction of pyridotriazoles with terminal alkynes; and cyclization of pyridines with three carbon fragments . Among these, 1,3-dipolar cycloaddition is very attractive because it can synthesize indolizines from simple substrates with high efficiency.…”

I2/FeCl3 Promoted Cascade Reaction of 4‐Quinazolinone, Pyridine, and Chalcone for the Synthesis of Indolizines

“…Consequently, continuous efforts have been made towards the synthesis of this type of molecules such as Tschitschibabin reaction, [21] Schmidt reaction, [22] 1,5 dipolar cyclization [23,24] and 1,3 dipolar cycloaddition of pyridinium methylides with electron‐poor alkynes or alkenes [25–27] . Issa Yavari and co‐workers in 2016 has been synthesized indolizines using FeCl 3 as a catalyst via the 1,3 dipolar cycloaddition between pyridinium ylide (Ylide of quinaldine and pyridine) and various chalcones (Scheme 1, A ) [28] . Issa Yavari & maryam naeimabadi in 2017 developed a method for the synthesis of indolizines via 1,3 dipolar cycloaddition between pyridinium N‐ylide and electron deficient alkyne in metal free reaction condition (Scheme 1, B ) [29] .…”

“…[25][26][27] Issa Yavari and co-workers in 2016 has been synthesized indolizines using FeCl 3 as a catalyst via the 1,3 dipolar cycloaddition between pyridinium ylide (Ylide of quinaldine and pyridine) and various chalcones (Scheme 1, A). [28] Issa Yavari & maryam naeimabadi in 2017 developed a method for the synthesis of indolizines via 1,3 dipolar cycloaddition between pyridinium N-ylide and electron deficient alkyne in metal free reaction condition (Scheme 1, B). [29] Recently our group developed synthesis of several heterocycles using multicomponent reaction [30][31][32][33] , here in this article, we have explored highly substituted indolizine derivatives through the 1,3-dipolar cycloaddition reaction of pyridinium methylide with substituted chalcone using an iron-metal catalyst.…”

Facile Synthesis of Indolizines via 1,3-Dipolar Cycloadditions in [Omim]Br: The Promotion of the Reaction through Noncovalent Interactions

“…Indolizines have diverse biological activities, − and photophysical properties, , and can be used as intermediates of other nitrogen heterocycles, , so many approaches have been developed for the synthesis of these compounds. − Among them, 1,3-dipolar cycloadditions of pyridinium ylides with unsaturated hydrocarbons are one of the most convergent and straightforward approaches toward functionalized indolizines. − Nevertheless, a major drawback of this method is that toxic, flammable, and volatile solvents such as DMF, THF, and CHCl 3 are often required, − which is obviously contrary to the principle of green chemistry. − Furthermore, the scope of unsaturated hydrocarbons and low-activity arylmethylpyridinium ylides is limited. Although several approaches for 1,3-dipolar cycloadditions from arylmethylpyridinium ylides have been explored, − the advances of these strategies have not performed well in the data. To solve these issues, we envisage the exploration of an efficient route for the formation of indolizines via 1,3-dipolar cycloadditions in green solvents.…”