Synthesis of polisubstituted 1,3-azadienes from enaminones

Synthesis of polisubstituted 1,3-azadienes from enaminones

Marques, Monique F.; Cunha, Silvio

Abstract:

Azadienes are considered useful building blocks to the synthesis of six-membered heterocyclic cores, mainly through the hetero Diels-Alder reaction. Olefination reactions such as Wittig’s, Julia’s, and Peterson’s are normally employed in order to obtain this class of compounds. As part of the reactivity study of azoenaminones (1) prepared by our research group, such compounds were treated with diverse electrophiles. Herein we present our results concerning the synthesis of 1,3-azadienes through acetylation reaction of azoenaminones, performed in mild conditions and with very good yields.

Azadienes are considered useful building blocks to the synthesis of six-membered heterocyclic cores, mainly through the hetero Diels-Alder reaction. Olefination reactions such as Wittig’s, Julia’s, and Peterson’s are normally employed in order to obtain this class of compounds. As part of the reactivity study of azoenaminones (1) prepared by our research group, such compounds were treated with diverse electrophiles. Herein we present our results concerning the synthesis of 1,3-azadienes through acetylation reaction of azoenaminones, performed in mild conditions and with very good yields.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013913141011

Referências bibliográficas

• [1] 1 Jayakumar, S.; Ishar, M.P.S.; Mahajan, M.P. Tetrahedron 2002, 58, 379.
• [2] 2 Barluenga, J.; Aznar, F.; Fustero, S.; Tomás, M. Pure And Appl. Chem.
• [3] 1990, 62, 1956.

Como citar:

Marques, Monique F.; Cunha, Silvio; "Synthesis of polisubstituted 1,3-azadienes from enaminones", p-227-227. 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_2013913141011