Síntese de pirazolinas graxas e pirazolo[1,5-d][1,2,4]triazin-4(5H)-ona
Resumo
Este trabalho descreve um método eficiente para a obtenção de
pirazolinas graxas e pirazolo-triazinona a partir da reação de ciclocondensação
[3+2] e [5+1]. Os compostos 4-alcoxi-1,1,1-trifluormetil-3-alquen-2-onas com
diferentes hidrazidas derivadas de ácidos graxos formam uma série de
pirazolinas graxas e o composto (E)-1,1,1-tricloro-4-etoxibut-3-en-2-ona é
utilizado como precursor na síntese de 1H-pirazol-5-carboidrazida que com
trietilortoformiato forma a pirazolo-triazinona, ambos os produtos são derivados
de pirazóis. A série de compostos de pirazolinas graxas foi obtida com bons
rendimentos que variaram de 70~87%. As estruturas de todos os compostos
sintetizados foram confirmadas por dados de Ressonância Magnética Nuclear
1
He C. Além destas análises, exclusivamente para a pirazolo-triazinona, foi
feito a difração de raios x de monocristal. Ao todo, nesta pesquisa, foram obtidos
16 compostos inéditos sendo possível aromatizar as pirazolinas graxas podendo
chegar a 31 compostos inéditos.
This work describes an efficient method to obtain pyrazolines and pyrazole-triazinone from the cyclocondensation reaction [3+2] and [5+1]. Compounds as 4-alkoxy-1,1,1-trifluoromethyl-3-alken-2-ones and different hydrazides derived from fatty acid form a series of fatty pyrazolines and the compound (E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one are used as a precursor in the synthesis of 1H-pyrazole-5-carbohydrazide which, with triethylorthoformate forms the pyrazolo-triazinone, both products are pyrazole derivatives. The series of fatty pyrazolines compounds were obtained in good yields ranging from 70~87%. The structures of all the synthesized compounds were confirmed by 1H and 13C Nuclear Magnetic Resonance data. Besides these analyzes, X-ray diffraction of monocrystal was made exclusively for pyrazolo-triazinone. Altogether, in this research, 16 unpublished compounds were obtained, being possible to aromatize the fatty pyrazolines, reaching 31 unpublished compounds.
This work describes an efficient method to obtain pyrazolines and pyrazole-triazinone from the cyclocondensation reaction [3+2] and [5+1]. Compounds as 4-alkoxy-1,1,1-trifluoromethyl-3-alken-2-ones and different hydrazides derived from fatty acid form a series of fatty pyrazolines and the compound (E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one are used as a precursor in the synthesis of 1H-pyrazole-5-carbohydrazide which, with triethylorthoformate forms the pyrazolo-triazinone, both products are pyrazole derivatives. The series of fatty pyrazolines compounds were obtained in good yields ranging from 70~87%. The structures of all the synthesized compounds were confirmed by 1H and 13C Nuclear Magnetic Resonance data. Besides these analyzes, X-ray diffraction of monocrystal was made exclusively for pyrazolo-triazinone. Altogether, in this research, 16 unpublished compounds were obtained, being possible to aromatize the fatty pyrazolines, reaching 31 unpublished compounds.
Descrição
Dissertação (Mestrado)
Palavras-chave
Ciclocondensação, Pirazolinas graxas, Pirazolo-triazinona, Cyclocondensation, Pyrazolines greases, Pyrazole-triazin
Citação
TEIXEIRA, Wystan Kreisly Othon. Síntese de pirazolinas graxas e pirazolo[1,5-d][1,2,4]triazin-4(5H)-ona. 2017. 81 f. Dissertação (Mestrado em Química Tecnológica e Ambiental) - Programa de Pós-graduação em Química Tecnológica e Ambiental, Escola de Química e Alimentos, Universidade Federal do Rio Grande, Rio Grande, 2017.