Synthesis of Cyclic Azo- and Hydrazo-Enaminones

Synthesis of Cyclic Azo- and Hydrazo-Enaminones

Marques, Monique Ferreira; Cunha, Silvio

Abstract:

Enaminones are precious synthetic intermediates in carbo and heterocycles synthesis, once they can be easily obtained and are densily functionalized with many reactive centers, which provides their ambiphilic and ambident behavior. Azo-enaminones are obtained through the incorporation of the azo group in the N-C=C-C=O conjugated system. The azo group plays an important role in the eletrooptics properties of these systems enhancing the structure planarity via an intramolecular hydrogen bonding and through its azo/hydrazo equilibrium. The planar conjugated π systems are necessary to a maximum push-pull conjugation and have important applications in second order nonlinear optical devices. Given the enaminones’ synthetic potential, our group decided to study these substances, developing new azo-enaminones.

Enaminones are precious synthetic intermediates in carbo and heterocycles synthesis, once they can be easily obtained and are densily functionalized with many reactive centers, which provides their ambiphilic and ambident behavior. Azo-enaminones are obtained through the incorporation of the azo group in the N-C=C-C=O conjugated system. The azo group plays an important role in the eletrooptics properties of these systems enhancing the structure planarity via an intramolecular hydrogen bonding and through its azo/hydrazo equilibrium. The planar conjugated π systems are necessary to a maximum push-pull conjugation and have important applications in second order nonlinear optical devices. Given the enaminones’ synthetic potential, our group decided to study these substances, developing new azo-enaminones.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0305-1

Referências bibliográficas

• [1] 1 Chemla, D.S.; Zyss, J. Nonlinear Optical Properties of Organic Molecules and Crystals; Academic Press: New York, 1987, Vols. I e II.
• [2] 2Lue, P.; Greenhill, J. V., Advances in Heterocyclic Chemistry; Katritzky, A. R., ed.; Academic Press: New York, 1997; Vol 67, pp 207-343.
• [3] 3Kuckländer, V., The Chemistry of Enamines; Rappoport, Z., ed.; John Wiley And Sons: New York, 1994; Part 1, pp 525-639.

Como citar:

Marques, Monique Ferreira; Cunha, Silvio; "Synthesis of Cyclic Azo- and Hydrazo-Enaminones", p-305-305. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0305-1