Organic letters

Microwave-assisted domino and multicomponent reactions with cyclic acylketenes: Expeditious syntheses of oxazinones and oxazindiones

M Presset, Y Coquerel, J Rodriguez

Index: Presset, Marc; Coquerel, Yoann; Rodriguez, Jean Organic Letters, 2009 , vol. 11, # 24 p. 5706 - 5709

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Citation Number: 53

Abstract

The microwave-assisted Wolff rearrangement of cyclic 2-diazo-1, 3-diketones in the presence of aldehydes and primary amines provides a straightforward access to functionalized bi-and pentacyclic oxazinones following an unprecedented three-component domino reaction. Alternatively, in the presence of acyl azides, an efficient Curtius/Wolff/hetero-Diels− Alder sequence allows the direct synthesis of oxazindiones.