Síntese de novas nitrocicloexanonas derivadas de dichalconas substituídas
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TCC
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2019-06
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Galvão, Bruna Corrêa
Oliveira, Welisson Vilarindo de
Oliveira, Welisson Vilarindo de
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Saavedra, Manuel Salustiano Almeida
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A síntese de novas dichalconas, de seus sais e de derivados como as 4-nitrocicloexanonas, é de imensa importância para a química orgânica pois são moléculas com alto potencial bioativo, alta conjugação e elevada reatividade, o que garante diversas aplicações. Os objetivos a serem alcançados neste trabalho visam a síntese de dichalconas e seus sais de sódio, com diferentes substituintes nos anéis aromáticos juntamente com a possibilidade de que esses compostos, sejam matérias primas para a síntese de 4-nitrocicloexanonas. Uma nova metodologia para a síntese de dichalconas substituídas foi adotada, sendo também a rota direta para a formação de seus respectivos sais. No trabalho foi demonstrado a efetividade da reação de adição Michael de nitrometano as dichalconas e seus sais na formação das 4-nitrocicloexanonas. Os dados espectrais juntamente com os Rf determinados na cromatografia de camada delgada (CCD) e os pontos de fusão, ratificam as estruturas dos compostos que foram sintetizados. Um fato interessante é o deslocamento a menor frequências da banda do grupo carbonila nos espectros infravermelhos das dichalconas pela alta conjugação que apresentam, quando comparado aos espectros das 4-nitrocicloexanonas sintetizadas de menor conjugação.
The synthesis of new dichalcones, their salts and derivatives such as 4-nitrocyclohexanones, is of immense importance for organic chemistry because they are molecules with high bioactive potential, high conjugation and high reactivity, which guarantees several applications. The objectives to be achieved in this work are the synthesis of dichalcones and their sodium salts, with different substituents in the aromatic rings together with the possibility that these compounds are materials raw for the synthesis of 4-nitrocyclohexanones. A new methodology for the synthesis of substituted dichalcones was adopted, being also the direct route for the formation of their respective salts. In the work the effectiveness of the Michael addition reaction of nitromethane and dichalcones and their salts in the formation of the 4-nitrocyclohexanones were demonstrated. The spectral data together with the Rf determined in thin layer chromatography (CCD) and melting points confirm the structures of the compounds that have been synthesized. An interesting fact is the shift at lower frequencies of the band of the carbonyl group in the infrared spectra of the dichalcones due to the high conjugation they present when compared to the spectra of the synthesized 4-nitrocycloananones of lower conjugation.
The synthesis of new dichalcones, their salts and derivatives such as 4-nitrocyclohexanones, is of immense importance for organic chemistry because they are molecules with high bioactive potential, high conjugation and high reactivity, which guarantees several applications. The objectives to be achieved in this work are the synthesis of dichalcones and their sodium salts, with different substituents in the aromatic rings together with the possibility that these compounds are materials raw for the synthesis of 4-nitrocyclohexanones. A new methodology for the synthesis of substituted dichalcones was adopted, being also the direct route for the formation of their respective salts. In the work the effectiveness of the Michael addition reaction of nitromethane and dichalcones and their salts in the formation of the 4-nitrocyclohexanones were demonstrated. The spectral data together with the Rf determined in thin layer chromatography (CCD) and melting points confirm the structures of the compounds that have been synthesized. An interesting fact is the shift at lower frequencies of the band of the carbonyl group in the infrared spectra of the dichalcones due to the high conjugation they present when compared to the spectra of the synthesized 4-nitrocycloananones of lower conjugation.
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síntese química , chalconas , dichalconas , 4-Nitrocicloexanonas , chemical synthesis , chalcones , dichalcones , 4-nitrocyclohexanone