3489-11-0

Upstream product

• 22812-12-0 6-methyl-4-oximinoflavan 
• 29976-75-8 6-methylflavone 
• 106-44-5 p-cresol 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 38445-23-7 6-methyl-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 536-74-3 phenylacetylene 
• 39513-75-2 6-methyl-4-chromanone 
• 1775-98-0 2'-hydroxy-5'-methylchalcone 
• 25268-01-3 3-(4-methylphenoxy)propanenitrile 
• 100-52-7 benzaldehyde 
• 1101612-88-7 C₂₁H₂₂O₄ 
• 121507-51-5 1-methyl-4-((1-phenylprop-2-yn-1-yl)oxy)benzene 

Downstream Products

• 1266399-34-1 8-methyl-4-phenyl-4H-benzopyran[4,3-d][1,2,3]selenadiazole 
• 118965-36-9 6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone 
• 1452877-06-3 [Co(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)22(NO₃)2] 
• 1452877-05-2 [Co(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2I₂] 
• 1452877-04-1 [Co(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Br₂] 
• 1452877-03-0 [Co(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Cl₂] 
• 1452877-13-2 [Cu(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)22(NO₃)2] 
• 1452877-12-1 [Cu(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Br₂] 
• 1452877-11-0 [Cu(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Cl₂] 
• 1452877-10-9 [Ni(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)22(NO₃)2] 
• 1452877-08-5 [Ni(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Br₂] 
• 1452877-07-4 [Ni(6-methyl-2-phenyl-4H-chromen-4-thiosemicarbazone)2Cl₂] 
• 37741-76-7 2-(1,5-diphenyl-1H-pyrazol-3-yl)-4-methylphenol 
• 1427025-15-7 (4E)-[(4-aminocarbonothioyl)hydrazono]-3,4-dihydro-6-methyl-2-phenyl-2H-1-benzopyran 

Relevant academic research and scientific papers

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.

An efficient and facile synthesis of flavanones catalyzed by N-methylimidazole

The use of N-methylimidazole as an efficient catalyst for the cyclization of 2'-hydroxychalcones to the corresponding flavanones in DMSO was investigated. The scope of this process was studied and various flavanones were obtained exclusively in good yields. Copyright

Simple and efficient one step synthesis of functionalized flavanones and chalcones

A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.

Asymmetric ion-pairing catalysis of the reversible cyclization of 2'-hydroxychalcone to flavanone: Asymmetric catalysis of an equilibrating reaction

The asymmetric catalytic cyclization of the simple 2'-hydroxychalcone (1) to flavanone (2), a model for the chalcone isomerase reaction, has been realized as a catalytic asymmetric ion-pairing process with chiral quaternary ammonium salts (e.g., 9-anthracenylmethlycinchoninium chloride; 9-Am-CN-Cl) and NaH as small-molecule co-catalyst. In toluene/CHCl3 solution, the process reaches an intrinsic enantioselectivity of up to S = 14.4 (er = 93.5:6.5). The reversible reaction proceeds in two steps: A fast initial reaction approaches a quasi-equilibrium with KR/S = 4.5, followed by a second, slow racemization phase approaching Krac = 9. A simple mechanistic model featuring a living ion-pairing catalysis with full reversibility is proposed. Deuterium transfer from co-solvent CDCl3 to product 2 and isolation of a Michael conjugate formed from 2 and 1 demonstrate the intermediacy of flavanone enolate ion pairs. A kinetic model shows good agreement with the experimentally observed, peculiar, time-dependent evolution of the species concentrations and the enantiomeric excess of 2. The reaction is a chemical model of the chalcone isomerase enzymatic reaction. Furthermore, it is an ideal model for studying the characteristic behavior of reversible asymmetric catalyses close to their equilibria.

Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones

The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst

Anhydrous potassium carbonate has been utilized as an inexpensive, safe, and efficient basic catalyst for the synthesis of flavanones starting either from 2′-hydroxychalcones or from 2′-hydroxyacetophenones. In both the cases the favored reaction condition was either refluxing in a solvent with added catalyst or microwave irradiation on the catalyst.