13787-96-7Relevant academic research and scientific papers
Hydrazones as Substrates in the Synthesis of Isoxazolidines via a KOH-Promoted One-Pot Three-Component Cycloaddition with Nitroso Compounds and Olefins
Chen, Wenwen,Li, Wenhui,Li, Xing,Lin, Jianying,Wei, Wen-Long,Zhai, Pingan
, p. 17710 - 17721 (2021/12/09)
Hydrazones have been employed as the starting materials in a KOH-mediated one-pot three-component cycloaddition with readily accessible nitroso compounds and olefins to construct various isoxazolidines. Compared with diazo compounds as starting materials, this methodology could afford a wider range of products in good to excellent yields and diastereoselectivities for most substrates, and hydrazones are cheaper, more accessible, and safer substrates. The experimental study shows that the choice of suitable hydrazones is crucial.
Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis
Shaum, James B.,Fisher, David J.,Sroda, Miranda M.,Limon, Luis,De Alaniz, Javier Read
, p. 8748 - 8752 (2018/12/10)
Synthetic chemists have spent considerable effort optimizing the synthesis of nitrogen and oxygen containing compounds through a number of methods; however, direct introduction of N- and O-functionality remains challenging. Presented herein is a general method to allow for the simultaneous installation of N- and O-functionality to construct unexplored N-O heterocyclic and amino-alcohol scaffolds. This transformation uses earth abundant copper salts to facilitate the formation of a carbon-centered radical and subsequent carbon-nitrogen bond formation. The intermediate aminoxyl radical is terminated by an intramolecularly appended carbon-centered radical. We have exploited this methodology to also access amino-alcohols with a range of aliphatic and aromatic linkers.
Conversion of nitrosobenzenes to isoxazolidines: An efficient cascade process utilizing reactive nitrone intermediates
Kang, Jun Yong,Bugarin, Alejandro,Connell, Brian T.
supporting information; experimental part, p. 3522 - 3524 (2009/02/05)
Reactive nitrones can be generated directly in situ by an unusual reaction of nitrosobenzene with styrene. The Royal Society of Chemistry.
Catalytic enantioselective inverse-electron demand 1,3-dipolar cycloaddition reactions of nitrones with alkenes
Simonsen,Bayon,Hazell,Gothelf,Jorgensen
, p. 3845 - 3853 (2007/10/03)
A general reaction protocol for catalytic enantioselective 1,3-dipolar cycloaddition reaction of nitrones, activated by chiral Lewis acids, with electron-rich alkenes has been developed. The nitrones are activated by various chiral 2,2'-dihydroxy-1,1'-binaphthyl (BINOL)-AlMe complexes, and it has been found that 3,3'-diaryl-BINOL-AlMe complexes catalyze a highly regio- , diastereo-, and enantioselective 1,3-dipolar cycloaddition reaction of aromatic nitrones with vinyl ethers, giving the exo-diastereomer of the isoxazolidines with de's up to > 90% and up to 97% ee. The reaction has been investigated under various conditions with different nitrones and vinyl ethers (and alkenes), and a general synthetic procedure is presented. The mechanism for the reaction is discussed on the basis of a linear stereochemical effect of the catalyst, the diastereoselectivity, and absolute stereochemistry of the isoxazolidines formed, and theoretical calculations of the 3,3'-diphenyl-BINOL-AlMe-nitrone intermediate.
Novel Catalytic System consisting of a 3,3'-Tetramethylene-bridged 4-Methylthiazolium Salt Leading to the Partial Reduction of Nitrobenzene with Benzaldehyde to a Nitrone
Inoue, Hiroo,Tamura, Shigeo
, p. 141 - 142 (2007/10/02)
A 3,3'-tetramethylene-bridged 4-methylthiazolium salt catalyses the reduction of nitrobenzene with benzaldehyde and triethylamine in methanol-water to give a nitrone.
