Studies on the ring opening reactions of 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones. Synthesis of aminomethyl oxazolidinones and aziridinyl ureas

Autor:	Jeffery A. Frick, Travis Dudding, Junfeng Huang, Abhijit Nayek, Stephen C. Bergmeier, Steven J. Katz, Lee Belding, Greggory M. Wells
Rok vydání:	2012
Předmět:	Reaction conditions Organic Chemistry Aziridine Ring (chemistry) Biochemistry Medicinal chemistry Solvent chemistry.chemical_compound chemistry Nucleophile Drug Discovery Urea Organic chemistry Amine gas treating Stoichiometry
Zdroj:	Tetrahedron. 68:3980-3987
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.03.071
Popis:	The reaction of fused ring aziridines, 3-oxa-1-azabicyclo[3.1.0]hexan-2-ones, with amine nucleophiles can provide either an aminomethyl oxazolidinone or an aziridinyl urea. The amine, reaction solvent, and aziridine substitution have been examined with the aid of computational studies to identify reaction conditions that provide a single product. Polar solvents provided only the aminomethyl oxazolidinone products. Formation of aziridinyl ureas required control of aziridine substitution, solvent, and reactant stoichiometry.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::44adf4f08b00f60c4c0666284439d9b8 https://doi.org/10.1016/j.tet.2012.03.071 Zobrazit plný text záznamu Full Text from ScienceDirect