Synthetic Studies Towards Arylpyrrole Derivatives via Heck- Matsuda Reaction

Synthetic Studies Towards Arylpyrrole Derivatives via Heck- Matsuda Reaction

Schwalm, Cristiane S.; Ferrari, Jailton; Correia, Carlos R. D.

Abstract:

The arylpyrrole unit is a widespread structural motif among biologically active compounds. For example, it is present on the structures of pyrrolnitrin (1), a potent antifungal agent, and pentabromopseudilin (2), which displays antibiotic, antitumor and lipoxygenase inhibitory activities (Figure 1). The Heck-Matsuda (HM) reaction employs arenediazonium salts as arylating agents and present several advantages over conventional protocols. It is a phosphine-free and air tolerant process. The more reactive nature of the arylating agent usually implies in shorter reaction times and milder reaction conditions. In this work we present the HM reaction as the key step in the synthesis of both 2 and 3-arylpyrroles, with applications in the synthesis of 2, isopentabromopseudilin 10 (its 3-aryl analogue) and 9 (a new 3-arylpyrrole derivative).

The arylpyrrole unit is a widespread structural motif among biologically active compounds. For example, it is present on the structures of pyrrolnitrin (1), a potent antifungal agent, and pentabromopseudilin (2), which displays antibiotic, antitumor and lipoxygenase inhibitory activities (Figure 1). The Heck-Matsuda (HM) reaction employs arenediazonium salts as arylating agents and present several advantages over conventional protocols. It is a phosphine-free and air tolerant process. The more reactive nature of the arylating agent usually implies in shorter reaction times and milder reaction conditions. In this work we present the HM reaction as the key step in the synthesis of both 2 and 3-arylpyrroles, with applications in the synthesis of 2, isopentabromopseudilin 10 (its 3-aryl analogue) and 9 (a new 3-arylpyrrole derivative).

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DOI: 10.5151/chempro-14bmos-R0019-1

Referências bibliográficas

• [1] 1 van Pée, K. H.; Ligon, J. M. Nat. Prod. Rep. 2000, 17, 157.
• [2] 2 Toste, F. D. et al. Org. Lett. 2005, 7, 2501.
• [3] 3 Taylor, J. G.; Moro, A. V.; Correia, C. R. D. Eur. J. Org. Chem. 2011, 1403.
• [4] 4 Knölker, H-J. et al.; Angew. Chem. Int. Ed. 2009, 48, 8042.

Como citar:

Schwalm, Cristiane S.; Ferrari, Jailton; Correia, Carlos R. D.; "Synthetic Studies Towards Arylpyrrole Derivatives via Heck- Matsuda Reaction", p-19-19. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0019-1