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N-Allyl-1,3-oxazines via a facile keto-ene/cyclization tandem reaction
Authors:Robert G Brinson
Affiliation:Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109, USA
Abstract:
The intramolecular keto-ene/cyclization tandem reaction of γ-N-allylamino ketones is an effective means of producing 1,3-oxazines. The reaction usually requires high temperatures and/or pressures. We discovered that N,N-diallyl amines undergo the reaction at lower temperatures than their monoallyl analogs. An extreme example, 1-N,N-diallylamino-9,10-anthraquinone, undergoes the keto-ene reaction near ambient temperature. In the case of 1-N,N′-dialkylaminoanthraquinones, electron deficient ene components can even be used, allowing the preparation of a broad spectrum of oxazines. Furthermore, the N-allyl-1,3-oxazine can be easily deallylated to produce a 1,3-oxazine that contains a secondary amine.
Keywords:Keto-ene   Tandem reaction   1,3-Oxazine   Anthraquinone
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