174153-62-9Relevant academic research and scientific papers
Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers
Thangaraj, Manikandan,Gaykar, Rahul N.,Roy, Tony,Biju, Akkattu T.
, p. 4470 - 4476 (2017/04/28)
A mild and transition-metal-free synthesis of β-keto arylthioethers has been developed by the aryne triggered [2,3] Stevens rearrangement of allylthioethers. The key sulfur ylide intermediate for the rearrangement was formed by the S-arylation of allylthi
2,3-Dihydro-1H-1,3-diazepin-2-ones: Synthesis and novel rearrangements into pyrrole derivatives
Fesenko, Anastasia A.,Shutalev, Anatoly D.
, p. 1416 - 1420 (2014/03/21)
A novel synthesis of 2,3-dihydro-1H-1,3-diazepin-2-ones based on thermal elimination of methanol from 4-methoxy-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones has been developed. The prepared dihydrodiazepinones underwent two new rearrangements under basic or
Synthesis of γ-azido-β-ureido ketones and their transformation into functionalized pyrrolines and pyrroles via staudinger/aza-wittig reaction
Fesenko, Anastasia A.,Shutalev, Anatoly D.
, p. 1190 - 1207 (2013/04/10)
A simple two-step procedure yielding γ-azido-β-ureido ketones or/and their cyclic isomers, 6-(1-azidoalkyl)-4-hydroxyhexahydropyrimidin-2- ones, has been developed. The synthesis includes three-component condensation of acetals of 2-azidoaldehydes with urea or methylurea and p-toluenesulfinic acid in aqueous formic acid followed by reaction of the obtained N-[(2-azido-1-tosyl) alkyl]ureas with sodium enolates of α-functionalized ketones. The azido ketones or their cyclic isomers are transformed into ureido-substituted Δ1- or/and Δ2-pyrrolines via Staudinger/aza-Wittig reaction promoted by PPh3. The obtained pyrrolines are converted into 3-functionalized 1H-pyrroles via elimination of urea under acidic conditions. Convenient one-pot syntheses of 1H-pyrroles starting from N-[(2-azido-1-tosyl)alkyl]ureas or γ-azido-β-ureido ketones have been also developed.
