33014-32-3

Upstream product

• 91-22-5 quinoline 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 74944-11-9 2-phenylimidazo[1,2-a]quinoline 
• 1227796-77-1 phenyl (pyrrolo[1,2-a]quinolin-1-yl)methanone 
• 1310066-81-9 1-benzoylpyrrolo[1,2-a]quinoline-2-carboxylic acid methyl ester 
• 1310066-83-1 1-benzoylpyrrolo[1,2-a]quinoline-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Indolizine quaternary ammonium salt inhibitors part II: A reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative

Phenacyl quinolinium bromide (PaQBr), an old-fashioned corrosion inhibitor in strong acid medium, was reinvestigated and a new indolizine derivative (DiPaQBr) was synthesized from PaQBr. DiPaQBr is classified as an indolizine quaternary ammonium salt. Bas

Nucleophilicity parameters of pyridinium ylides and their use in mechanistic analyses

Kinetics of the reactions of pyridinium, isoquinolinium, and quinolinium ylides with diarylcarbenium ions, quinone methides, and arylidene malonates (reference electrophiles) have been studied in dimethylsulfoxide solution by UV-vis spectroscopy. The seco

Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines

An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cycloisomerization is proposed.

Ultrasound-promoted regioselective synthesis of chalcogeno-indolizines by a stepwise 1,3-dipolar cycloaddition

A series of new organochalcogen derivatives of indolizines was synthesized in moderate to excellent yields from pyridinium salts and chalcogeno-alkynes. The reaction can be carried out under thermal conditions or by sonochemical processes in short reaction times. The stepwise cycloaddition reaction forming chalcogeno-indolizines is regioselective and extends to a broad range of functional groups. Furthermore, novel chalcogeno-alkynes are reported and the first derivatives of teluro-indolizine are described. The influence of selenium functionalization on the photophysical properties of indolizines is also described, in which the compounds showed absorption in the UV–Vis region around 360 nm and emission in the blue-to-green region. Relatively low fluorescence quantum yield (?fl) values were calculated, in agreement with the chalcogen effect on other heterocycles.

DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes

With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the -Br group which can be further transformed to other functionalities by cross-coupling reactions. The modular feature of o-AQM substrates and the simple operation procedures add further advantages to this synthetic method.

New quinoline- and isoquinoline-based multicomponent methods for the synthesis of 1,1(3,3)-dicyanotetrahydrobenzoindolizines

Convenient multicomponent methods for the synthesis of benzannulated dihydroindolizines based on quinoline or isoquinoline, malononitrile, aromatic aldehydes and α-halomethylcarbonyl compounds were developed. Several alternative protocols of using the reactants were studied, starting with separate generation of two most probable intermediates and ending with the four-component condensation of all reactants. The scope of applicability of these methods was found, depending on the initial compounds used. The reaction is highly stereoselective with predominant formation of one of the possible isomers.

DABCO-catalyzed multi-component domino reactions for the one-pot efficient synthesis of diverse and densely functionalized benzofurans in water

An efficient, three-component strategy for the improved synthesis of a pharmaceutically interesting diverse kind of multi-functionalized benzofurans via one-pot two-step domino protocol with high diastereoselectivity in excellent yields has been established. The synthesis was achieved by reacting phenacyl bromides, N-heterocycles, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of DABCO (1,4-diazabicyclo[2.2.2]octane) as an inexpensive, impressive, and readily available catalyst in water under reflux. In this process in total three new bonds (two C–C and one C–O) form in one pot. Short reaction time, excellent yields, no chromatographic purification, and evasion of environmentally hazardous or toxic catalysts and organic solvents in the entire reaction process may make this protocol very useful for academia and industry.

Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant

A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.

Amberlite-IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1,2-a] quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products

A number of indolizines and pyrrolo[1,2-a]quinolines/isoquinolines were prepared from phenacyl pyridinium, quinolinium and isoquinolinium salts derived fromthe reaction of the heterocycles with 2-bromo acetophenone with alkynes and alkenes using amberlite-IRA-402 (OH) ion exchange resin as the base. Antibacterial and antifungal studies were carried out against thirteen bacterial and four fungal strains, which revealed that three derivatives (4a, 4b, 7a) out of fifteen are effective against all the thirteen strains and one derivative, 10, showed dual antibactericidal and antifungal efficacy.

Preparation of 1-trifluoroacetyl indolizines and their derivatives via the cycloaddition of pyridinium N-ylides with 4-4-ethoxy1-1,1,1-trifluorobut-3-en-one

Under basic reaction conditions pyridinium or isoquinolinium N-ylides (C5H5N+ CH2YBr- or C9H7N+CH2YBr-, Y : CO2R, CN, PhCO) reacted readily with 4-ethoxyl-1,1,1-trifluorobut-3-en-2-one to give the corresponding 1-trifluoroacetyl substituted indolizines or pyrrolo-[1,2-a]isoquinolines. The molecular structure of 1-trifluoromethyl-3-methoxyl-pyrrolo-[1,2-a]isoquinoline is presented.