SYNTHESIS AND REACTIVITY OF ALPHA-ALLENYLHYDROXYLAMINES - A NEW EFFICIENT ACCESS TO 3,6-DIHYDRO-1,2-OXAZINES

Authors
DUMEZ E DULCERE JP
Citation
E. Dumez et Jp. Dulcere, SYNTHESIS AND REACTIVITY OF ALPHA-ALLENYLHYDROXYLAMINES - A NEW EFFICIENT ACCESS TO 3,6-DIHYDRO-1,2-OXAZINES, Chemical communications, (4), 1998, pp. 479-480
Citations number
54
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
4
Year of publication
1998
Pages
479 - 480
Database
ISI
SICI code
1359-7345(1998):4<479:SAROA->2.0.ZU;2-F
Abstract
SmI2-promoted reduction of alpha-allenyl nitro derivatives 2a-f using controlled conditions provides either 3-amino-4-vinylidenetetrahydrofu ran 3a or 3-hydroxylamino-4-vinylidenetetrahydrofurans 4b-f, which und ergo intramolecular cyclization consistent with a reverse Cope elimina tion to afford 3,6-dihydro-1,2-oxazines 5b-f.