Directed Functionalization of Quinoxalines Aiming the Synthesis of Bioactive Compounds

Directed Functionalization of Quinoxalines Aiming the Synthesis of Bioactive Compounds

Ferreira, Samuel R. A.; Pena, Jesus M.; Silva, Simone C.; Clososki, Giuliano C.

Abstract:

Access to functionalized organometallic compounds has increased considerably the scope of these nucleophilic reagents in organic synthesis. Directed metalation using mixed lithium-magnesium bases as TMPMgCl.LiCl are widely used for a smooth metalations of several aromatics and heterocycles with a good functional group compatibility. However, deprotonation of substituted quinoxalines gave unsatisfactory results due to the high reactivity of the intermediate magnesium species. Herein, we wish to report a direct method for the deprotonation and functionalization of some substituted quinoxalines by using TMPMgCl.LiCl in the presence of ZnCl2.

Access to functionalized organometallic compounds has increased considerably the scope of these nucleophilic reagents in organic synthesis. Directed metalation using mixed lithium-magnesium bases as TMPMgCl.LiCl are widely used for a smooth metalations of several aromatics and heterocycles with a good functional group compatibility. However, deprotonation of substituted quinoxalines gave unsatisfactory results due to the high reactivity of the intermediate magnesium species. Herein, we wish to report a direct method for the deprotonation and functionalization of some substituted quinoxalines by using TMPMgCl.LiCl in the presence of ZnCl2.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391317050

Referências bibliográficas

• [1] 1 Wanderlich, S. H., Rohbogner, C. J., Unsinn, A., Knochel, P. Organic Process Research and Development. 2010, 339, 345.
• [2] 2 Dong, Z. Clososki, G.C. Wunderlich, S. H. Unsinn, A. Li, Jinshan. Knochel, P. Chem. Eur. J. 2009, 15, 457.

Como citar:

Ferreira, Samuel R. A.; Pena, Jesus M.; Silva, Simone C.; Clososki, Giuliano C.; "Directed Functionalization of Quinoxalines Aiming the Synthesis of Bioactive Compounds", p-75-75. 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_201391317050