New Aza-pterocarpan Analogues by Intramolecular 1,3-Dipolar Cycloaddition in in situ generated nitroneolefins

New Aza-pterocarpan Analogues by Intramolecular 1,3-Dipolar Cycloaddition in in situ generated nitroneolefins

Barcellos, Julio C. F.; Dias, Ayres G.; Costa, Paulo R. R.

Abstract:

As part of a program aiming the synthesis of new compounds with anticancer and antiparasitic action, we recently synthesized aza-pterocarpans such as 1 and 2 (Figure 1). Compound 1 showed significant activity against cancer cell lines and Leshimania. In order to have more information on the structureactivity relationship in this new class of prototypes, we decided to prepare compounds type 3. In this communication we describe the stereoselective synthesis of these analogues via intramolecular 1.3-dipolar cycloaddition (1,3DCI) in nitrones (4) prepared from salicylaldehyde derivatives (5) and hydroxiamines (6). These precursors can be prepared and isolated or, more conveniently, generated in situ.

As part of a program aiming the synthesis of new compounds with anticancer and antiparasitic action, we recently synthesized aza-pterocarpans such as 1 and 2 (Figure 1). Compound 1 showed significant activity against cancer cell lines and Leshimania. In order to have more information on the structureactivity relationship in this new class of prototypes, we decided to prepare compounds type 3. In this communication we describe the stereoselective synthesis of these analogues via intramolecular 1.3-dipolar cycloaddition (1,3DCI) in nitrones (4) prepared from salicylaldehyde derivatives (5) and hydroxiamines (6). These precursors can be prepared and isolated or, more conveniently, generated in situ.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013820154447

Referências bibliográficas

• [1] 1 Buarque, C.D. et al. Bioorg. Med. Chem 2011, 19, 6885..
• [2] 2 Preciding communication..
• [3] 3Cheng Q. et al. J. Chem. Soc., Perkin Trans. 1, 2001, 452.
• [4] 4Broggini G., Zecchi C. Synthesis, 1996, 1280.

Como citar:

Barcellos, Julio C. F.; Dias, Ayres G.; Costa, Paulo R. R.; "New Aza-pterocarpan Analogues by Intramolecular 1,3-Dipolar Cycloaddition in in situ generated nitroneolefins", p-187-187. 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_2013820154447