19958-60-2Relevant academic research and scientific papers
Synthesis of N-acetoxy-N-arylamides via diacetoxyiodobenzene promoted double acylation reaction of hydroxylamines with aldehydes
Zhang, Huaiyuan,Su, Yingpeng,Wang, Ke-Hu,Huang, Danfeng,Li, Jun,Hu, Yulai
supporting information, p. 5337 - 5344 (2017/07/10)
A facile and efficient synthesis of N-acetoxy-N-arylamides through double acylations of hydroxylamines with aldehydes and diacetoxyiodobenzene is reported. The yields of the products are good to excellent.
Reaction of aromatic nitroso compounds with chemical models of 'thiamine active aldehyde'
Ferreira, Luísa M.,Marques, M. Manuel B.,Glória, Paulo M.C.,Chaves, Humberto T.,Franco, Jo?o-Pedro P.,Mourato, Isabel,Antunes, José-Rafael T.,Rzepa, Henry S.,Lobo, Ana M.,Prabhakar, Sundaresan
, p. 7759 - 7770 (2008/12/21)
Aromatic nitroso compounds in the presence of base and 2-(α-hydroxyalkyl)-3,4-dimethylthiazolium trifluoromethanesulfonate and related salts furnish in variable yields O- and N-acyl-aryl hydroxylamines and 3,4-dimethylthiazolium trifluoromethanesulfonate. A primary kinetic isotope effect of 4.9, obtained for the appropriate 2α-deuterated thiazolium salt, points to the C2α-H bond cleavage as the rate determining step. Radical species detected by ESR were unambiguously identified as phenylhydronitroxide, but attempted trapping of the corresponding C-heterocyclic radicals by TEMPO was not successful, and substrates incorporating a potential cyclopropyl radical clock gave products with the cyclopropyl ring intact. Theoretical calculations revealed a large activation energy for such reaction, which thus cannot per se exclude the intervention of such radical species. Evidence for the likely operation of two concurrent mechanisms, a radical and a preponderant ionic pathway, involving the conjugate base of the thiazolium salt, as the chemical model for 'active thiamine', and ArNO is presented for the formation of the products of the reaction.
Reactions of 2-acylthiazolium salts with N-arylhydroxylamines
Ferreira, Luisa M.,Lobo, Ana M.,Prabhakar, Sundaresan,Teixeira, Antonieta C.
, p. 3541 - 3552 (2007/10/03)
2-Acylthiazolium salts, easily obtained by alkylation of the corresponding 2-acylthiazoles with methyl triflate, react with N- arylhydroxylamines to furnish the O-acyl derivatives of relevance in the induction of cancer by aromatic mines.
Selective O-acylation of aromatic hydroxylamines by 2-acylimidazolium and 2-acylbenzimidazolium salts
Santos, Pedro P. O.,Trindade, Cristina L.,Lobo, Ana M.,Prabhakar, Sundaresan
, p. 3793 - 3796 (2007/10/02)
2-Acyl 1,3-dimethylbenzimidazolium and 2-acyl 1,3-dimethylimidazolium salts react with N-aromatic hydroxylamines in the presence of base to give the O-acyl derivatives.
