71027-98-0Relevant articles and documents
Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines
Mehedi, Md Shafaat Al,Tepe, Jetze J.
, p. 7219 - 7226 (2019/06/14)
This work describes an extended version of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react with the sulfur ylides to provide imidazolines.
Copper-catalyzed oxidative desulfurization-promoted intramolecular cyclization of thioamides using molecular oxygen as an oxidant: An efficient route to five- To seven-membered nitrogen-containing heterocycles
Shibahara, Fumitoshi,Yoshida, Atsunori,Murai, Toshiaki
, p. 646 - 647 (2008/12/21)
Copper-catalyzed oxidative desulfurization-promoted intramolecular cyclization reactions of thioamides take place under neutral and mild conditions by using molecular oxygen as an oxidant. The process yields a wide variety of nitrogen-containing heterocyc
A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors
Groundwater, Paul W.,Garnett, Ian,Morton, Andrew J.,Sharif, Toqir,Coles, Simon J.,Hursthouse, Michael B.,Nyerges, Miklos,Anderson, Rosaleen J.,Bendell, David,McKillop, Alexander,Zhang, Weimin
, p. 2781 - 2787 (2007/10/03)
The synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors was presented. The nitrile ylides were prepared by the 1,3-dehydrochlorination of imidoyl chlorides. It was shown that the HOMO of the 'bent' nitrile ylide is heavily localized on the methane terminus and is compatible with protonation at this carbon in substituted nitrile ylides and with the regioisomers obtained in biomolecular nitrile ylide cycloadditions. The observed regiochemistry of the cycloaddition was rationalized by energy calculations on the frontier molecular orbitals of the reactants using semi-empirical methods.
