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Synlett 1997; 1997(2): 173-174
DOI: 10.1055/s-1997-735
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Synthesis of Heterocyclic Quinones by Aza-Diels-Alder Reaction of a 4-Stannyl-1-azadiene

Juan M. Cuerva, Antonio M. Echavarren*
  • *Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
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Publication History

Publication Date:
31 December 2000 (online)

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4-Stannyl-1-azadiene 2 undergoes aza-Diels-Alder reactions with activated dienophiles. Selective oxidation of the adducts proceeds with allylic inversion allowing for the efficient preparation of new heterocyclic quinones.

[4+2]cycloaddition - N,N-dimethylhydrazones - azaquinones - organostannanes - benzo[g]quinolinetrione