Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones

Autor:	Bart Vanderhoydonck, Christian V. Stevens
Rok vydání:	2007
Předmět:	chemistry.chemical_compound chemistry Dimethyl sulfoxide Methyl chloroformate Organic Chemistry Drug Discovery Organic chemistry Regioselectivity Aziridine Ring (chemistry) Biochemistry
Zdroj:	Tetrahedron. 63:7679-7689
ISSN:	0040-4020
DOI:	10.1016/j.tet.2007.05.023
Popis:	Syntheses of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones were achieved from the corresponding 1-vinyl-2-phosphonoaziridines. Regioselective aziridine ring opening employing methyl chloroformate affords 1-amido-2-chloroethylphosphonates, which were easily transformed into the corresponding 2-oxazolidinones upon heating in dimethyl sulfoxide. Treatment of the aziridine ring opening products with ammonia furnishes vinylphosphonates, which undergo a Michael type addition with several amines. In situ ring closure of the addition products yields the corresponding phosphonylated 2-imidazolidinones.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::128de757025369e4eb43c5e19b3fb302 https://doi.org/10.1016/j.tet.2007.05.023 Zobrazit plný text záznamu Full Text from ScienceDirect