Formation of quinoxaline monoxides from reaction of benzofurazan oxide with enones and carbon-13 NMR correlations of quinoxaline N-oxides

AF Kluge, ML Maddox, GS Lewis

Index: Kluge, Arthur F.; Maddox, Michael L.; Lewis, Graham S. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1909 - 1914

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Citation Number: 28

Abstract

Benzofuran oxide (1) reacts with a variety of enones and amines to give quinoxaline monoxides. The nature of the amine determines the regiochemistry of the product: secondary amines give a type 4 product and primary amines give a type 5 product. Reaction of 1, cinnamaldehyde, and morpholine gave both 4a and 8a. The regiochemistry of these N- oxide products is discussed in terms of intermediate 11. Principal limitations of these ...