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Synlett 2000; 2000(7): 1028-1030
DOI: 10.1055/s-2000-6651
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A Straightforward Synthetic Pathway to Phenanthro[9,10-d]heterocycles

Roberto Olivera* , Raúul SanMartin, Esther Domínguez
  • *Kimika Organikoa Saila, Zientzi Fakultatea, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain; Fax + 34 94 464 8500; E-mail: qopdopee@lg.ehu.es
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Publication Date:
31 December 2000 (online)

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A series of new 4,5-o,o-bis(haloaryl)pyrazoles was regioselectively prepared by a tandem amine exchange/heterocyclization. The intramolecular Stille-type biaryl coupling of the so-obtained pyrazole derivatives and previously prepared diarylisoxazoles led with high overall yields to the isolation of new phenanthro[9,10-d]pyrazoles and phenanthro[9,10-d]isoxazoles, respectively. The formation of dehalogenation products was efficiently avoided by use of heavy-wall pressure tubes.

isoxazoles - pyrazoles - Stille biaryl coupling