1,4-Addition of organolithium compounds to 6-ethoxy-3-phenyl-6H-1,2-oxazine

Authors
Zimmer, R Hiller, F Reissig, HU
Citation
R. Zimmer et al., 1,4-Addition of organolithium compounds to 6-ethoxy-3-phenyl-6H-1,2-oxazine, HETEROCYCLE, 50(1), 1999, pp. 393-401
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
1
Year of publication
1999
Pages
393 - 401
Database
ISI
SICI code
0385-5414(19990101)50:1<393:1OOCT6>2.0.ZU;2-4
Abstract
Addition of organolithium compounds to 6-ethoxy-3-phenyl-6H-1,2-oxazine (1) proceeds in conjugate fashion generating 4-lithiated 1,2-oxazines. After t rapping with various electrophiles 1,2-oxazines (2 - 9) were generally isol ated in good yields and with predominant 4,5-trans/5,6-trans-arrangement of the newly introduced substituents. Scope and limitations of this new route to tetrasubstituted 1,2-oxazines are discussed.