Diastereoselective synthesis of dihydroquinolines and tetrahydroquinolines from Morita Baylis-Hillman adducts

Diastereoselective synthesis of dihydroquinolines and tetrahydroquinolines from Morita Baylis-Hillman adducts

Jr., Manoel T. Rodrigues; Agy, Andre Capretz; Lustosa, Danilo Machado; Coelho, Fernando

Abstract:

The quinolone, dihydroquinolines and tetrahydroquinolines unities are present in many natural and synthetic compounds. These nuclei exhibit a wide spectrum of medicinal properties, such as antimalarial, antitumor, antibacterial, antithrombin, and many others. Due to this biological profile several synthetic approaches have been known for the preparation of these heterocycles. In this work we disclosed a facile method to prepare quinolines derivatives through a Morita-Baylis- Hillman adduct. Our approach is based on a tandem sequence involving a Michael addition reaction and a SNAr reaction.

The quinolone, dihydroquinolines and tetrahydroquinolines unities are present in many natural and synthetic compounds. These nuclei exhibit a wide spectrum of medicinal properties, such as antimalarial, antitumor, antibacterial, antithrombin, and many others. Due to this biological profile several synthetic approaches have been known for the preparation of these heterocycles. In this work we disclosed a facile method to prepare quinolines derivatives through a Morita-Baylis- Hillman adduct. Our approach is based on a tandem sequence involving a Michael addition reaction and a SNAr reaction.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013820154052

Referências bibliográficas

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• [3] 3 Coelho, F.; Almeida, W. P.; Mateus, C. R.; Feltrin, M.; Costa, A. M.
• [4] Tetrahedron 2001, 57, 6901. 4. Rodrigues Jr., M. T.; Gomes, J. C.; Smith,
• [5] J.; Coelho, F. Tetrahedron Lett. 2010, 51, 4988.

Como citar:

Jr., Manoel T. Rodrigues; Agy, Andre Capretz; Lustosa, Danilo Machado; Coelho, Fernando; "Diastereoselective synthesis of dihydroquinolines and tetrahydroquinolines from Morita Baylis-Hillman adducts", p-186-186. 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_2013820154052