Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides

Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides

Santos, Airam O.; Correia, José Tiago Menezes; Cunha, Silvio

Abstract:

Fused bicyclic heterocycles with a bridgehead nitrogen atom is a structural scaffold present in various natural and unnatural bioactive compounds. Among these heterocycles, the pyrrolizidines, indolizidines and pyrroloazepines are important classes of alkaloids from the medicinal chemistry and chemical ecology point of views. We disclosure herein our results concerning the formal aza-[3+2] and formal aza-[3+3] cycloaddition reactions of cyclic enaminones, including a chiral one, with maleic anhydride and N-aryl-maleimides, wherein pyrrolizidines, indolizidines and pyrroloazepines could be selectively obtained.

Fused bicyclic heterocycles with a bridgehead nitrogen atom is a structural scaffold present in various natural and unnatural bioactive compounds. Among these heterocycles, the pyrrolizidines, indolizidines and pyrroloazepines are important classes of alkaloids from the medicinal chemistry and chemical ecology point of views. We disclosure herein our results concerning the formal aza-[3+2] and formal aza-[3+3] cycloaddition reactions of cyclic enaminones, including a chiral one, with maleic anhydride and N-aryl-maleimides, wherein pyrrolizidines, indolizidines and pyrroloazepines could be selectively obtained.

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DOI: 10.5151/chempro-14bmos-R0315-1

Referências bibliográficas

• [1] 1 Ferraz, H. M. C. e Pereira, F. L. C. Quim. Nova 2004, 27, 89.
• [2] 2 Das, B.; Veukateswarlu, K.; Majhi, A.; Ravinder, M. R.; Reddy, K. N.; Rao, Y. K.; Kavikumar, K. e Sridhar, B. J. Mol. Cat. A: Chemical 2006, 246, 276-281.
• [3] 3 Nagaka, T.; Inoue, H.; Ichimura, M.; Hamaguchi, F. Synthesis, 1982, 10, 848

Como citar:

Santos, Airam O.; Correia, José Tiago Menezes; Cunha, Silvio; "Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides", p-315-315. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0315-1