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Synlett 2000; 2000(5): 0689-0691
DOI: 10.1055/s-2000-6618
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(o-Trifluoroacetamido)cinnamaldehyde Dimethylhydrazone, a Useful Azadiene in the Hetero Diels-Alder Approach to the Pyrido[2,3,4-kl]acridine System

Ma del Mar Blanco* , Carmen Avendaño, J. Carlos Menéndez
  • *Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain; Fax 34-91-394 18 22; E-mail: josecm@eucmax.sim.ucm.es
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Publication Date:
31 December 2000 (online)

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The hetero Diels-Alder reaction between (o-trifluoroacetamido)cinnamaldehyde dimethylhydrazone and several quinones followed by aromatization and hydrolytic cyclization afforded the corresponding pyrido[2,3,4-kl]acridine derivatives in 26-43% overall yields.

Diels-Alder reactions - quinolines - quinones - marine natural products - pyridoacridines