21978-65-4Relevant articles and documents
Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
Shen, Xuanyu,Shatskiy, Andrey,Chen, Yan,K?rk?s, Markus D.,Wang, Xiang-Shan,Liu, Jian-Quan
, p. 3560 - 3567 (2020/03/04)
A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.
Ketene. Part 21. Reactions of Heterocumulenes with Nitrones
Evans, Andrew R.,Hafiz, Mushtaq,Taylor, Giles A.
, p. 1241 - 1246 (2007/10/02)
Degradative and mass spectrometric evidence confirms the formation of the isoxazolidinones (2) from the reaction of cyano-t-butylketene with the N-alkyl nitrones (1), whilst the reaction with the N-phenyl nitrone (1d) gives the expected oxazolidinone (3b).Cyano-t-butylketene reacts with diphenyl nitrone to give the indolones (10a) and (10b).The reaction of phenyl isocyanate with diphenyl nitrone, and the N-alkyl nitrones (1a) and (1d) gives the normal 1,3-dipolar cycloadducts without rearrangement.Ethoxycarbonyl-t-butylketene reacts with the N-phenyl nitrone (1d) to give an oxazolidinone , but reaction with the N-alkyl nitrones (1) gives only fluorenone azine.This ketene reacts with diphenyl nitrone to give the anil (15) and the dihydroindole (16).