Synthesis of Aza-Pterocarpan Analogues via 1,3 Intramolecular Dipolar Cycloadditions in in situ generated Iminoolefins

Synthesis of Aza-Pterocarpan Analogues via 1,3 Intramolecular Dipolar Cycloadditions in in situ generated Iminoolefins

C.F.Barcellos, Julio; Dias, Ayres G.; Sansano, José M.; Nájera, Carmen; Costa, Paulo R. R.

Abstract:

As part of a program directed towards the discovery of new compounds with anticancer and antiparasitic action, we recently synthesized azapterocarpans such as 1 (Figure 1), through a aza- Heck palladium catalyzed reaction. This substance showed significant activity against strains of cancer and Leshimania. Here, dipolar cycloaddition (1,3-DCI) of imines (3) were made. These intermediates were generate in situ by reaction of salicylaldehydes (4a,b) with the amino acids glycine (5a), alanine and phenylalanine (5b,c) (used as racemates, we describe the synthesis of new derivatives of 1, of type 2 (analogs of 1) through intramolecular 1,3) and the amino diethyl malonate (5d).

As part of a program directed towards the discovery of new compounds with anticancer and antiparasitic action, we recently synthesized azapterocarpans such as 1 (Figure 1), through a aza- Heck palladium catalyzed reaction. This substance showed significant activity against strains of cancer and Leshimania. Here, dipolar cycloaddition (1,3-DCI) of imines (3) were made. These intermediates were generate in situ by reaction of salicylaldehydes (4a,b) with the amino acids glycine (5a), alanine and phenylalanine (5b,c) (used as racemates, we describe the synthesis of new derivatives of 1, of type 2 (analogs of 1) through intramolecular 1,3) and the amino diethyl malonate (5d).

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DOI: 10.5151/chempro-15bmos-BMOS2013_20131017134836

Referências bibliográficas

• [1] 1Buarque, C.D. et al. Bioorganic And Medicinal Chemistry 2011, 19, 6885.
• [2] 2Bashiardes G., et al. Organic Letters, 2003, 25, 4915.

Como citar:

C.F.Barcellos, Julio; Dias, Ayres G.; Sansano, José M.; Nájera, Carmen; Costa, Paulo R. R.; "Synthesis of Aza-Pterocarpan Analogues via 1,3 Intramolecular Dipolar Cycloadditions in in situ generated Iminoolefins", p-307-307. 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_20131017134836