Direct, two-step synthetic pathway to novel dibenzo[a,c]phenanthridines

Fátima Churruca; Raul SanMartin; Mónica Carril; Miren Karmele Urtiaga; Xavier Solans; Imanol Tellitu; Esther Domínguez

doi:10.1021/jo0501036

Direct, two-step synthetic pathway to novel dibenzo[a,c]phenanthridines

J Org Chem. 2005 Apr 15;70(8):3178-87. doi: 10.1021/jo0501036.

Authors

Fátima Churruca¹, Raul SanMartin, Mónica Carril, Miren Karmele Urtiaga, Xavier Solans, Imanol Tellitu, Esther Domínguez

Affiliation

¹ Kimika Organikoa II Saila, Zientzi eta Teknologia Fakultatea, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain.

PMID: 15822980
DOI: 10.1021/jo0501036

Abstract

Novel dibenzo[a,c]phenanthridines are prepared regioselectively by the application of a straightforward synthetic pathway, starting from new 3,4-diaryl- and 3,4-dihydro-3,4-diarylisoquinolines prepared via Ritter-type heterocyclization and the more classical two-step reductive amination/Bischler-Napieralski cyclization of triarylethanones, respectively. A comparative study of nonphenolic oxidative coupling methodologies provides a highly efficient procedure, based on the hypervalent iodine reagent phenyliodine(III) bis(trifluoroacetate) (PIFA), to accomplish the final coupling step.