Tetrahedron letters

N-Allyl-1, 3-oxazines via a facile keto-ene/cyclization tandem reaction

RG Brinson, PB Jones

Index: Brinson, Robert G.; Jones, Paul B. Tetrahedron Letters, 2004 , vol. 45, # 32 p. 6155 - 6158

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Citation Number: 2

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 ...