Synthesis of isobenzofuranones by Diels-Alder reaction

Synthesis of isobenzofuranones by Diels-Alder reaction

Teixeira, Milena G.; Alvarenga, Elson S.; Demuner, Antonio J.; Maltha, Célia R. A.; Barbosa, Luiz Claudio A.

Abstract:

Phthalides or isobenzofuranones are fused γ- lactones with an aromatic ring which have attracted the attention of many research groups because of their wide spectrum of activity as antifungal, antibacterial, antiviral, etc. The α,β-unsaturated lactones are found as structural subunits in a wide variety of natural products possessing diverse biological activities. Furthermore, simple lactones have been used as intermediates for the synthesis of biologically active compounds. In the present work we have synthesized 9-carbon lactones with structures similar to natural phthalides through Diels- Alder (DA) reaction. For this goal, furan-2(5H)-one has acted as an excellent dienophile in cycloaddition reactions with cyclopentadiene.

Phthalides or isobenzofuranones are fused γ- lactones with an aromatic ring which have attracted the attention of many research groups because of their wide spectrum of activity as antifungal, antibacterial, antiviral, etc. The α,β-unsaturated lactones are found as structural subunits in a wide variety of natural products possessing diverse biological activities. Furthermore, simple lactones have been used as intermediates for the synthesis of biologically active compounds. In the present work we have synthesized 9-carbon lactones with structures similar to natural phthalides through Diels- Alder (DA) reaction. For this goal, furan-2(5H)-one has acted as an excellent dienophile in cycloaddition reactions with cyclopentadiene.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013910132953

Referências bibliográficas

• [1] 1 Logrado, L. P. L. et al. European Journal of Medicinal Chemistry 2010,
• [2] 45, 3480.
• [3] 2 Sardan, M.; Sezer, S.; Gunel, A.; Akkaya, M.; Tanyeli, C. Bioorg. Med.
• [4] Chem. Lett 2012, 22, 5814.

Como citar:

Teixeira, Milena G.; Alvarenga, Elson S.; Demuner, Antonio J.; Maltha, Célia R. A.; Barbosa, Luiz Claudio A.; "Synthesis of isobenzofuranones by Diels-Alder reaction", p-205-205. 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_2013910132953