4198-15-6Relevant academic research and scientific papers
Short and efficient route toward α-substituted N-arylazetidines from acetanilides via Mitsunobu reaction
Kern, Nicolas,Hoffmann, Marie,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
, p. 5519 - 5531 (2015/03/30)
N-Arylazetidines are efficiently obtained in a three-step procedure, providing a wide diversity of derivatives on multigram scale with overall yields of 21-55%. Cheap or easily available acetanilides are used in an adapted aldolization with aldehydes, fur
Amide synthesis by nucleophilic attack of vinyl azides
Zhang, Feng-Lian,Wang, Yi-Feng,Lonca, Geoffroy Herve,Zhu, Xu,Chiba, Shunsuke
supporting information, p. 4390 - 4394 (2014/05/06)
A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide. Nitrilium intermediate: A new method for amide synthesis employs vinyl azides as enamine-type nucleophiles towards carbon electrophiles in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate A migrates to form nitrilium ion B, which is hydrolyzed to afford the corresponding amide.
Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols
Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
supporting information; experimental part, p. 1961 - 1966 (2010/06/20)
"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.
Facile reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by an aqueous TiCl3/NH3 system: Selectivity and scope
Clerici, Angelo,Pastori, Nadia,Porta, Ombretta
, p. 3326 - 3335 (2007/10/03)
A simple and rapid procedure for the almost quantitative reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by use of TiCl3/NH3 in aqueous methanol solution is reported. The reducing system distinguishes between different classes of aldehydes and/or ketones, and many functionalities that usually do not survive under reducing conditions are tolerated well. The concept of reversal of chemoselectivity has also been developed. A mechanism based on two sequential one-electron transfers from TiIII to the carbonyl carbon atom is proposed, the second SET becoming operative only in the presence of ammonium ion (either added or formed in situ). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Organotellurium Chemistry. 7. Reductive Removal of Electronegative α Substituents of Ketones and Acids by a Tellurolate Reagent
Engman, Lars,Cava, Michael P.
, p. 3946 - 3949 (2007/10/02)
Lithium and sodium 2-thiophenetellurolates have been used for the reductive dehalogenation of a variety of α-halo ketones and acids.Acetoxy, mesyloxy, and phenylthio groups were also successfully removed from the α position of an acetophenone.The reductions could in many cases be carried out by using sodium borohydride as the reducing agent in the presence of only a catalytic amount of the organotellurium reagent.Evidence is presented in support of a two-step mechanism involving the formation of α-aryltelluro carbonyl derivatives and enolate anions in succession.
