61161-26-0Relevant articles and documents
A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles
Ieronimo, Gabriella,Palmisano, Giovanni,Maspero, Angelo,Marzorati, Alessandro,Scapinello, Luca,Masciocchi, Norberto,Cravotto, Giancarlo,Barge, Alessandro,Simonetti, Marco,Ameta, Keshav Lalit,Nicholas, Kenneth M.,Penoni, Andrea
supporting information, p. 6853 - 6859 (2018/10/20)
A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.
Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions
Jurok, Radek,Hodacova, Jana,Eigner, Vaclav,Dvorakova, Hana,Setnicka, Vladimir,Cibulka, Radek
supporting information, p. 7724 - 7738 (2013/12/04)
A series of substituted planar chiral flavinium salts with a phenyl "cap" have been prepared as potential catalysts for enantioselective sulfoxidation reactions with hydrogen peroxide by using an approach based on the synthesis of (arylamino)uracils and their condensation with substituted nitrosobenzenes. The effect of substituents at various positions on the ability of the catalyst to promote enantioselective sulfoxidation recations was investigated. Introduction of the tyrosine group into the side-chain of the flavinium species or substitution of the nitrogen N-3 of the flavin unit by o-isopropylphenyl has a remarkably positive effect on the enantioselectivity of the sulfoxidation reactions of aromatic and aliphatic substrates, respectively. On the other hand, substitution of the phenyl "cap" led to a substantial decrease in the efficiency of the catalyst. In summary, optimisation of the structures of the planar chiral flavinium catalysts led to enantioselectivities of up to 61 % ee for aromatic sulfides and of up to 65 % ee for tert-butyl methyl sulfide. By making structural changes to the planar chiral flavinium catalysts, the enantioselectivities of the sulfoxidation of aryl methyl sulfides and tert-butyl methyl sulfide with hydrogen peroxide have been improved. Copyright
Preparation and study of chemical transformations of N-formyl-N-phenylhydroxylamines
Guilbaud-Criqui, A.,Moinet, C.
, p. 164 - 172 (2007/10/02)
Nitrosobenzenes with CO2H 1b, CO2CH3 3b and CON(CH3)C6H5 4b ortho-substituents were obtained in a "redox" cell from the corresponding nitro compounds.In order to prepare the 3-oxo-1,2-dihydro-2,1-benzisoxazole-1-carbaldehyde from o-substituted N-formyl-N-phenylhydroxylamines, nitroso derivatives were formylated by glyoxylic acid.The N-formylbenzisoxazolone is unstable in the reaction medium and cannot be isolated.In addition to our study, we showed the unstability of N-formyl-N-phenylhydroxylamines and N-formylanilines in the presence of methanol without acetic acid; in an aqueous methanolic medium, formylation of nitrosoderivatives is equivalent to a reduction of the nitroso group.The mechanism was demonstrated by formylation of the nitrosobenzene and the electrogenerated 2-nitrosobenzene acetic acid 2b.Key Words: flow cell electrosynthesis / nitrosobenzenes / glyoxylic acid / formylation / N-formyl-N-phenylhydroxylamines / N-formylanilines / benzisoxazolones
