Benzocarbazolquinones and Benzonaphthofurandiones by Palladium Catalyzed Oxidative C-H Functionalization

Benzocarbazolquinones and Benzonaphthofurandiones by Palladium Catalyzed Oxidative C-H Functionalization

Lisboa, Cinthia da Silva; Santos, Gustavo dos; Lucas, Nanci C. de; Garden, Simon J.

Abstract:

Quinones are very interesting compounds not only because of their bright colours but also because of their diverse biological properties for example in the treatment of: tuberculosis, malaria, bacterial and parasitic infections and as antineoplastics. Within a program investigating C-H functionalization reactions we recently described improved methodology for the oxidative coupling of anilines with naphthoquinone. Additionally, we have now studied the oxidative cyclization (formation of a C-C bond from two C-H bonds) of 2-anilino- and 2- phenyloxy- naphthoquinones.

Quinones are very interesting compounds not only because of their bright colours but also because of their diverse biological properties for example in the treatment of: tuberculosis, malaria, bacterial and parasitic infections and as antineoplastics. Within a program investigating C-H functionalization reactions we recently described improved methodology for the oxidative coupling of anilines with naphthoquinone. Additionally, we have now studied the oxidative cyclization (formation of a C-C bond from two C-H bonds) of 2-anilino- and 2- phenyloxy- naphthoquinones.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013819114414

Referências bibliográficas

• [1] 1. a) Thomson, R. H.; Editor Naturally Occurring Quinones IV: Recent
• [2] Advances, 4th Edition; Blackie: London, UK, 1997. b) Macías-Ruvalcaba,
• [3] N., Cuevas, G., González, I., Aguilar-Martínez, M. J. Org. Chem. 2002, 67,
• [4] 3673. c) Jakeman, D. L.; Farrell, S.; Young, W.; Doucet, R. J.; Timmons, S.
• [5] C. Bioorg. Med. Chem. Lett. 2005, 15, 1447-9. d) del Corral, J. M. M.,
• [6] Castro, M. A., Gordaliza, M., Martín, M. L., Gamito, A. M., Cuevas, C.,
• [7] Feliciano, A. S. Bioorg. Med. Chem. 2006, 14, 2816.
• [8] 2. Lisboa, C. S.; Santos, V. G.; Vaz, B. G.; de Lucas, N. C.; Eberlin, M. N.;
• [9] Garden, S. J. J. Org. Chem. 2011, 76, 5264.
• [10] 3. For example see: a) Echavarren, A. M., Tamayo, N., Paredes, C.
• [11] Tetrahedron Lett. 1993, 34, 4713. b) Knoelker, H.-J., O'Sullivan, N.
• [12] Tetrahedron 1994, 50, 10893. c) Hagelin, H., Oslob, J. D., Akermark, B.
• [13] Chem. Eur. J. 1999, 5, 2413. d) Liégault, B., Lee, D., Huestis, M. P., Stuart,
• [14] D. R., Fagnou, K. J. Org. Chem. 2008, 73, 5022.

Como citar:

Lisboa, Cinthia da Silva; Santos, Gustavo dos; Lucas, Nanci C. de; Garden, Simon J.; "Benzocarbazolquinones and Benzonaphthofurandiones by Palladium Catalyzed Oxidative C-H Functionalization", p-168-168. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013819114414