36377-40-9

Upstream product

• 16883-69-5 N-phenacylpyridinium bromide 
• 110-86-1 pyridine 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 

Downstream Products

• 85574-80-7 1-acetyl-3-benzoyl-2-hydroxyindolizine 
• 97204-08-5 (1R,2R,3S,8aR)-3-Benzoyl-1,2,3,8a-tetrahydro-indolizine-1,2-dicarbonitrile 
• 97204-08-5 (1S,2S,3S,8aR)-3-Benzoyl-1,2,3,8a-tetrahydro-indolizine-1,2-dicarbonitrile 
• 68980-62-1 1-Benzoyl-4,5,6,7-tetraphenylspiro<2.4>-4,6-heptadien 
• 90625-64-2 E-1,2,3-tribenzoylpropene 
• 35134-01-1 4-benzoyl-2,6-diphenylpyridine 
• 90625-61-9 3-[2-Oxo-2-phenyl-eth-(E)-ylidene]-1-p-tolyl-pyrrolidine-2,5-dione 
• 90625-60-8 3-(2-oxo-2-phenyl-ethylidene)-1-phenyl-pyrrolidine-2,5-dione 
• 86551-92-0 C₃₇H₂₆N₂O₂ 

Relevant academic research and scientific papers

Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition

An ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2- b ]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.

Electrophilicities of 1,2-disubstituted ethylenes

The kinetics of the reactions of maleic anhydride, N-methylmaleimide, fumaronitrile, diethyl fumarate, and diethyl maleate with pyridinium and sulfonium ylides were studied in DMSO at 20 C. All of the reactions were found to follow a second-order rate law

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

Regioselective CH bond activation on stabilized nitrogen ylides promoted by Pd(II) complexes: Scope and limitations

The orthopalladation of N-ylides [HxCyN-CHC-(O)Ar] (HxCyN = pyridine, benzylamine, imidazole, aniline, and phenylpyridine; Ar = aryl) has been studied. The incorporation of the Pd atom to these substrates is regioselective, since the orthopalladation is produced, in most of the cases, only at the aryl ring of the benzoyl group with concomitant C-bonding of the Nylide. The X-ray structure of one representative example is reported. Factors governing the observed orientation are discussed, because this regioselectivity is worthy of note, considering the deactivating nature of the carbonyl group. Two exceptions to the general trend have been observed. The first one is the double metalation of the ylide [PhMe2NCHC(O)Ph], which incorporates one Pd at each Ph. The second one is the palladation of the phenylpyridine derivative, which occurs at the pyridinic 2-phenyl ring and produces a six-membered palladacycle.

Synthesis of tetrasubstituted pyridazines via cascade reactions of diazocarbonyl compounds with pyridinium ylides

Reactions of pyridinium ylides with diazocarbonyl compounds involve the formation of functionalized azine intermediates that can undergo intramolecular cyclocondensation into tetrasubstituted pyridazines provided the starting reagents contain carbonyl groups. Reactions of pyridinium ylides with diazo compounds were studied for various substituents in both the substrates.

Pyridinium Ylides in Syntheses of Naphthopyrandiones and in Regioselective Syntheses of Acylated Anthraquinones Related to Fungal and Bacterial Metabolites

Improvements have been made in the use of acylated pyridinium ylides for the transformation of 2-methyl-1,4-naphthoquinone into derivatives (15) and (16) of naphthopyran-5,10-dione, containing furan and thiophene groups.The substitution and cyclisation steps can be combined effectively by using 2-phenoxymethyl- instead of 2-methyl-naphthoquinone.The use of better leaving groups than phenoxy (especially 4-nitrophenoxy) allows the quinone to react with two proportions of ylide and leads regiospecifically to 1-aroyl-2-arylanthracene-9,10-diones such as (20a).If the leaving group is nuclear bromine as in 2-bromo-3-methyl-1,4-naphthoquinone, another reaction with 2 mol equiv. of ylide leads to complex red intermediates of type (31) which in contact with alumina are quantitatively converted into the regioisomeric 2-aroyl-3-arylanthracene-9,10-diones such as (22a).The structures have been determined by standard methods but special features of the NMR spectra are reported including a case of extreme line broadening by traces of iron.Mechanisms are suggested for the diverse reactions between the quinones and the ylides.