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2004
Oxazine derivatives
R 0595
N-Allyl-1,3-oxazines via a Facile Keto-ene/Cyclization Tandem Reaction. —
ketones (III), (V) and (VII) undergo intramolecular keto-ene/cycliza46- 157 γ-N-Allylamino
tion tandem reaction to give the corresponding N-allyl-1,3-oxazines. Compared to usually high temperatures and/or pressures, the allylamino anthraquinones (III) react
already at temperatures ≤ 55 °C. As is exemplified for (VIa), the N-allyl group can be
removed under mild conditions. In addition, a similar keto-ene cyclization occurs with
the alkene intermediate in the one-pot conversion of (X) to the oxazine (XII). —
(BRINSON, R. G.; JONES*, P. B.; Tetrahedron Lett. 45 (2004) 32, 6155-6158; Dep.
Chem., Wake Forest Univ., Winston-Salem, NC 27109, USA; Eng.) — Roy
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