Síntese regiosseletiva de 4- Aril (Heteroaril)- 2-Azido Pirimidinas Trifluorometiladas e aplicação na preparação de 4- Aril (Heteroaril)-2-(4-Fenil-1H-1,2,3-Triazol-1-il) -6-(Trifluorometil) Pirimidinas

Abstract

Este trabalho descreve o estudo da reatividade do 5-Aminotetrazol frente a 1,1,1-trifluormetil-4-metoxi-3-alquen-2-onas, obtidas pelo método da acilação de acetais, na produção de 5- aril (heteroaril) - 2-azido Pirimidinas Trifluorometiladas (3a- f), e derivatização via reações Click, obtendo os compostos 4- R- 2- (4- fenil- 1H- 1,2,3-triazol- 1-il) -6- (trifluorometil) pirimidinas (5a-e) e4-R-2-Amino Pirimidina Trifluorometilada 6, obtida pela redução da azida promovida pelo ascorbato de sódio. Obteve-se as 2-Azida-4-R-6- (Trifluormetil) Pirimidinas com bom rendimento e de forma pura, sendo que o composto 2-Azida-4-Fenil-6- (Trifluormetil) Pirimidina foi analisado por Espectroscopia de Raio X comprovando a estrutura na forma tautomérica da azida. Com análises de Espectroscopia de Infravermelho para os compostos (3a- f) observou-se as bandas de absorção características do grupo azida. A obtenção dos 4- R- 2- (4- fenil- 1H- 1,2,3-triazol- 1-il) -6- (trifluorometil) pirimidinas (5a-e) e 4-R-2-Amino Pirimidina Trifluorometilada 6 se deu com bons rendimentos, utilizando Sulfato de Cobre e Ascorbato de Sódio como catalisadores.

This work describes the reactivity of 5-Aminotetrazol to 1,1,1-trifluoromethyl-4-methoxy-3-alken-2-ones, obtained by the acetyl acylation method, in the production of 5-aryl (heteroaryl) Trifluoromethylated pyrimidines (3a- f), and derivatised via Click reactions, yielding the compounds 4-R-2- (4-phenyl-1H-1,2,3-triazol-1-yl) -6- ( trifluoromethyl) pyrimidines (5a- e) and 4-R-2-Amino-Pyrimidine Trifluoromethylated 6 obtained by reduction of the azide promoted by Sodium Ascorbate. 2-Azide-4-R-6- (Trifluoromethyl) -pyrimidines were obtained in good yield and in pure form, 2-Azide-4-Phenyl-6- (Trifluoromethyl) -pyrimidine Compound was analyzed by Ray Spectroscopy X confirming the structure in the tautomeric form of the azide. With infrared spectroscopy analyzes for the compounds (3a- f) the absorption bands characteristic of the azide group were observed. Preparation of 4-R-2- (4-phenyl-1H-1,2,3-triazol-1-yl) -6- (trifluoromethyl) pyrimidines (5a-e) and 4R-2-Amino Pyrimidine Trifluoromethylated 6 was produced in good yields using Copper Sulfate and Sodium Ascorbate as catalysts.