A more efficient entry to phenanthridinone

Nerea Conde; Fátima Churruca; Raul SanMartin; María Herrero; Esther Domínguez

doi:10.3390/MOL2NET-02-H002

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A more efficient entry to phenanthridinone

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¹ Department of Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Bilbao, Spain.

Published: 05 February 2016 by MDPI in MOL2NET'16, Conference on Molecular, Biomed., Comput. & Network Science and Engineering, 2nd ed. congress CHEMBIOMOL-02: Chem. Biol. & Med. Chem. Workshop, Rostock, Germany-Bilbao, Spain-Galveston, Texas, USA, 2016

https://doi.org/10.3390/MOL2NET-02-H002

Abstract:

The presence of the phenanthridinone core in natural products and biologically active compounds has encouraged research on more efficient approaches to such valuable tricyclic framework.[1] Due to the lack of transmetallating agents and the atom-economy implied, palladium-catalyzed direct arylation is an appealing alternative for the ring closure step. However, the relative high amount of the catalyst employed may become a serious drawback from a practical view.[2] In this context, we wish to present the application of a palladacyclic complex to this reaction and the significant reduction of the catalytic amount achieved (0.05 mol%) in the successful preparation of a series of phenanthridinone derivatives.

[1] Bhakuni, B. S.; Kumar, A.; Balkrishna, S. J.; Sheikh, J. A.; Konar, S.; Kumar, S. Org. Lett. 2012, 14, 2838-2841.

[2] Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692-10705.

Keywords: Phenanthridinones; Transmetallating agents; Palladium-catalyzed direct arylation

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