92976-86-8

Upstream product

• 1122-58-3 dmap 
• 70-11-1 α-bromoacetophenone 
• 99834-10-3 C₁₅H₁₆N₂O 

Downstream Products

• 99834-10-3 C₁₅H₁₆N₂O 
• 113816-27-6 C₂₀H₁₂O₄ 
• 624-49-7 dimethylfumarate 
• 17372-52-0 4,6-diphenyl-2H-pyran-2-one 
• 29261-44-7 4,6-diphenyl-2-pyridone 

Relevant academic research and scientific papers

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.

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.

Unexpected reactivity of pyridinium salts toward alkynyl Fischer complexes to produce oxo-heterocycles

The unprecedented reaction of ketone-containing aromatic pyridinium salts 3a-e and alkynyl Fischer complexes 1a-f proceeds via a mild domino process to provide 4,6-disubstituted pyran-2-ones 5a-k and 2,3,5-trisubstituted furans 6a-h (45-97%). According of the results of isotopic labeling experiments, a mechanism involving an initial Michael addition appears to be the key step, obtaining a mesomeric structure responsible for the formation of both products.

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

Copper acetate monohydrate: A cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes

We report a highly practical one-pot method for synthesizing multi-substituted indolizines from ?±-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.

1-Phenacyl-, 1-carbethoxymethyl-and 1-benzyl-4-dimethylaminopyridinium halides: Isolation and use for generating ylide

Active halide containing electron withdrawing group (EWG) α - to halogen readily reacts with 4-dimethylaminopyridine (DMAP) to give stable salt of pyridinium halide (1-6). The reaction between 1-phenacyl-4dimethylaminopyridinium halide(s) (1 and 2) and aq

Hydrogen-bonded (H2O·X)2 [X=Cl-, Br-] clusters in 1-phenacyl-4-(dimethylamino)pyridinium halide monohydrates

The synthesis, and X-ray crystal and molecular structures, of 1-phenacyl-4-(dimethylamino)pyridinium chloride and bromide monohydrates are described.

Experimental and quantum chemical evidences for C-H···N hydrogen bonds involving quaternary pyridinium salts and pyridinium ylides

The rates of equilibrium of eight quaternary pyridinium salts containing activated methylene groups with the corresponding ylides have been measured in DMSO solution containing strong bases (DBU, MTBD and P1-tBu). The effect of the ring substituents on th

Kinetic and theoretical studies on the reaction of phenacyl bromide with 4DMAP in the presence of certain phenols

The quaternization reaction between phenacyl bromide and 4-(dimethylamino)pyridine (4DMAP) has been studied at 25, 30 and 35°C in acetone. Added phenols with pKa > 7.0 retard the rate of quaternization and there is no ether formation. This has