83188-10-7

Upstream product

• 614-47-1 1,3-diphenyl-propen-3-one 
• 1083-30-3 dihydrochalcone 
• 94-41-7 benzalacetophenone 
• 13411-48-8 1-(trimethylsilyl)ethanone 
• 431-03-8 dimethylglyoxal 
• 75-07-0 acetaldehyde 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 83188-05-0 3-diethylamino-1,3-diphenyl-propan-1-one 
• 917-54-4 methyllithium 
• 148868-87-5 enol acetate of 3-phenylpropiophenone 
• 6277-76-5 4-nitro-1,3-diphenyl-pentan-1-one 
• 93319-08-5 1-acetoxy-1,2-diphenylcyclopropane 

Downstream Products

• 16206-35-2 3,5-diphenyl-2-methyl-1H-pyrrole 
• 56138-25-1 2-methyl-3,5-diphenyl furan 
• 110466-56-3 2-Methyl-3,5-diphenyl-3,4-dihydro-2H-pyrrol-2-ol 

Relevant academic research and scientific papers

Thiazolium-functionalized polystyrene monolithic microreactors for continuous-flow umpolung catalysis

Thiazolium salt pre-catalysts have been immobilized on silica and monolithic polystyrene and their activity was tested under batch conditions in three model umpolung reactions, namely the benzoin condensation of benzaldehyde, the acyloin-type condensation of biacetyl, and the Stetter reaction of biacetyl with trans-chalcone. A prerequisite of the study has been the utilization of environmentally benign water and ethanol solvents. After having established the higher performance of polystyrene monolithic thiazolium carbene catalysts, their effectiveness has been tested under the flow regime by fabricating the corresponding monolithic microreactors (pressure-resistant stainless-steel columns). Importantly, it has been demonstrated by a brief substrate scope study that the polymeric matrix and the continuous flow regime synergistically contribute to preserve the activity of the carbene catalysts over time, thus permitting the long-term operation (up to 7 days) of the prepared monolithic reactors for the production of valuable compounds via the umpolung strategy.

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones

An efficient method for the N-heterocyclic carbene (NHC)-catalyzed conjugate addition of acetyl anions to various α,β-unsaturated acceptors (Stetter reaction) has been optimized by using 2,3-butandione (biacetyl) as an alternative surrogate of acetaldehyde. The disclosed procedure proved to be compatible with microwave dielectric heating for reaction time reduction and with the use of different linear α-diketones as acyl anion donors (e.g. 3,4-hexanedione for propionyl anion additions). Moreover, the unprecedented umpolung reactivity of cyclic α-diketones in the atom economic nucleophilic acylation of chalcones is herein presented. Mechanistic aspects of the thiazolium-based catalysis involving linear and cyclic α-diketone substrates are also discussed. The Royal Society of Chemistry 2011.

Enone-alkyne reductive coupling: A versatile entry to substituted pyrroles

The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dica

N-Heterocyclic carbene-catalysed intermolecular Stetter reactions of acetaldehyde

A facile method for the intermolecular Stetter reaction of various Michael acceptors with acetaldehyde as a biomimetic acylanion source was realized using N-heterocyclic carbene catalysis. This catalytic system has also been applied to the enantioselective Stetter reaction and resulted in moderate to good enantioselectivities for the corresponding Stetter products.

THERAPEUTIC COMPOUNDS FOR DISEASES AND DISORDERS

Pyrrole derivatives are disclosed as agents for the treatment and prevention of neuropathies and neurodegenerative diseases characterized by the presence of axonal blockages, impaired axonal transport or impaired trafficking of vesicles in neurons.

PYRROLE DERIVATIVES AS THERAPEUTIC COMPOUNDS

Novel pyrrole derivatives are disclosed as Aβ42-lowering agents for the treatment and prevention of neurodegenerative disorders characterized by the formation or accumulation of amyloid plaques comprising the Aβ42 peptide.

Photorearrangement and electron transfer photooxidation of 1-acetoxy-1,2-diphenylcyclopropane

Direct irradiation of the title compound 4 in hexane led to 1,3-diphenyl-1,4-pentanedione (5) in 75 % yield. This is explained through carbonyl-oxygen bond cleavage (process iii), to afford a cyclopropyloxy radical (I) which rearranges to a β-carbonyl radical (II) prior to in cage recombination. In methanol, the solvent addition product 6 was obtained as byproduct. It formation is rationalized by means of the symmetrical cationic intermediate IV, on the basis of deuterium incorporation to C(1) and C(3) in MeOD. Photosensitization by acetone resulted exclusively in trans to cis isomerization, via the diradical III (process i). Finally electron transfer activation by means of cerium(IV) ammonium nitrate (CAN) or excited triphenylpyrylium tetrafluoroborate (TPT) gave rise to chalcone (7) or the β-functionalized ketones 8 or 9. These products must arise from a common cationic precursor (V), after cleavage of the central carbon-carbon bond (process i) in the radical cation 4+. From the preparative point of view, the obtention of diketone 5 in 75% yield by photolysis of 4 in hexane is exploitable, since it constitutes a synthetic equivalent of the addition of acyl anions or acyl radicals to enones.

THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 12. ISOLATION OF INTERMEDIATE 2-HYDROXY-3,4-DIHYDRO-2H-PYRROLES IN THE PAAL-KNORR 1H-PYRROLE SYNTHESIS.

Treatment of 1,4-diketones with liquid ammonia gives high yields of isolable 2-hydroxy-3,4-dihydro-2H-pyrrole intermediates.These intermediates, which do not appear to have been observed previously in the Paal-Knorr synthesis with ammonia, have been fully characterized by i.r. and 1H and 13C n.m.r. spectroscopy; in most cases they decompose quantitatively into 1H-pyrroles on standing.The intermediate from hexane-2,4-dione may also be prepared using concentrated aqueous ammonia.

A NOVEL PHOTOCHEMICAL 1,4-ACYL MIGRATION IN ENOL ESTERS. THE PHOTOLYSIS OF ENOL ACETATES OF 3-PHENYLPROPIOPHENONES

Photolysis of the enol acetates 1a, b gives the 1,4-diketones 4a, b by a mechanism involving a primary homolytic carbonyl-oxygen bond cleavage, followed by 1,2-hydrogen shift and in cage recombination.

(Phosphine)carbonylnitrosylacylcobaltate Complexes as Acyl Transfer Reagents. Acylation of Allylic Halides, Conjugated Enones, and Quinones

The complex Co(NO)(CO)2(PPh3) is an air stable, easily handled crystalline solid, prepared from Co2(CO)8, sodium nitrite, and triphenylphosphine without isolation of the volatile intermediate Co(NO)(CO)3.Treatment of this complex with organolithium reagents at -40 deg C generated unstable acylate complexes - which readily transferred the acyl group to allylic halides to produce β,γ-unsaturated ketones, to conjugated ketones to produce 1,4-dicarbonyl compounds, and to quinones to form 4-acylcyclohexadienones.