132448-51-2Relevant academic research and scientific papers
A Revised Mechanism for the Kinugasa Reaction
Malig, Thomas C.,Yu, Diana,Hein, Jason E.
, p. 9167 - 9173 (2018)
Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in nitrone and alkyne, respectively. Furthermore, the reaction displays a second-order dependence on the catalyst, confirming the critical involvement of a postulated bis-Cu complex. Finally, reaction progress analysis of multiple byproducts has allowed a new mechanism, involving a common ketene intermediate to be delineated. Our results demonstrate that β-lactam synthesis through the Kinugasa reaction proceeds via a cascade involving (3 + 2) cycloaddition, (3 + 2) cycloreversion, and finally (2 + 2) cycloaddition. Our new mechanistic understanding has resulted in optimized reaction conditions to dramatically improve the yield of the target β-lactams and provides the first consistent mechanistic model to account for the formation of all common byproducts of the Kinugasa reaction.
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.
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.
