14674-32-9Relevant academic research and scientific papers
Catalytic asymmetric synthesis of dihydroquinazolinones from imines and 2-aminobenzamides
Cheng, Dao-Juan,Tian, Yu,Tian, Shi-Kai
supporting information; experimental part, p. 995 - 999 (2012/06/01)
An unprecedented catalytic asymmetric synthesis of aminal-containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β- unsaturated, and aliphatic imines react with 2-aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N-substituent through non-bonding interactions with the chiral phosphoric acid and the 2-aminobenzamide. Copyright
Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
, p. 2000 - 2005 (2007/10/02)
A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
