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Title: Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones
Authors: Vanderhoydonck, Bart
Stevens, Christian # ×
Issue Date: 23-May-2007
Publisher: Pergamon Press
Series Title: Tetrahedron vol:63 issue:32 pages:7679-7689
Abstract: 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 Me chloroformate affords 1-amido-2-chloroethylphosphonates, which were easily transformed into the corresponding 2-oxazolidinones upon heating in DMSO. Treatment of the aziridine ring opening products with ammonia furnishes vinylphosphonates, which undergo a Michael type addn. with several amines. In situ ring closure of the addn. products yields the corresponding phosphonylated 2-imidazolidinones.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Non-KU Leuven Association publications
× corresponding author
# (joint) last author

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