83948-45-2Relevant academic research and scientific papers
Synthesis of NH-3-phenylsulfanyl- and NH-3-benzylsulfanyl-azetidinones from 1-phenylsulfanyl- or 1-benzylsulfanyl-3-aza-1,3-dienes
Panunzio, Mauro,Bongini, Alessandro,Tamanini, Emiliano,Campana, Eileen,Martelli, Giorgio,Vicennati, Paola,Zanardi, Ilaria
, p. 9577 - 9582 (2003)
The syntheses of NH-3-phenylsulfanyl- and NH-3-benzylsulfanyl-azetidinones, starting from 1-phenylsulfanyl- or 1-benzylsulfanyl-2-trimethylsilyloxy-3-aza- 1,3-dienes are reported.
Hetero-Diels-Alder (HDA) strategy for the preparation of 6-aryl- and heteroaryl-substituted piperidin-2-one scaffolds: Experimental and theoretical studies
Long, Sha,Monari, Magda,Panunzio, Mauro,Bandini, Elisa,D'Aurizio, Antonio,Venturini, Alessandro
experimental part, p. 6218 - 6225 (2011/12/01)
Preparation of piperidine-2-one scaffolds by the hetero-Diels-Alder (HAD) reaction, assisted by microwaves, is described. The versatility of this new approach has been demonstrated by the synthesis of racemic (±)-2- phenylpiperidine. Theoretical calculati
N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams
Ha, Deok-Chan,Hart, David J.,Yang, Teng-Kuei
, p. 4819 - 4825 (2007/10/02)
Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams.The stereochemical course of the reaction depends on the ester enolate geometry.Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams.The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis.The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-imine condensations are also discussed.
Preparation of Primary Amines and 2-Azetidinones via N-Trimethylsilyl Imines
Hart, David J.,Kanai, Ken-ichi,Thomas, Dudley G.,Yang, Teng-Kuei
, p. 289 - 294 (2007/10/02)
Nonenolizable aldehydes react with lithium bis(trimethylsilyl)amide at ambient temperatures to afford solutions of N-trimethylsilyl aldimines.Treatment of these solutions with Grignard reagents or alkyllithiums followed by an aqueous workup gives primary amines in moderate to excellent yields.Treatment of N-trimethylsilyl aldimines with ester enolates provides an expedient route to 1-unsubstituted 2-azetidinones.
