Synthesis of 7-trifluo[trichlo]romethyl-5-aryl[alkyl]-tetrazolo[1,5-a] pyrimidines in Ionic Liquid

Synthesis of 7-trifluo[trichlo]romethyl-5-aryl[alkyl]-tetrazolo[1,5-a] pyrimidines in Ionic Liquid

Scapin, Elisandra; Buriol, Lilian; Frizzo, Clarissa Piccinin; Martins, Marcos A. P.

Abstract:

Tetrazolopyrimidines are important biological agents with a wide range of pharmaceutical (e.g., hyperlipidemia, depression, glaucoma, and cardiac arrhythmias) and agrochemical uses. The synthesis of this class of compounds by cyclocondensation reaction requires extreme conditions such as the use of acids, high temperatures, and prolonged reaction times. Another drawback for obtaining these compounds is the low yields. Furthermore, the synthesis of trifluoromethylated tetrazolopyrimidine from trifluoromethylated substrates is very limited. The incorporation of fluorine into a drug allows simultaneous modulation of electronic, lipophilic, and steric parameters, all of which can critically influence both the pharmacodynamic and pharmacokinetic properties of drugs. In this work, we develop a simple and convenient protocol for the direct synthesis of 7- trifluo(trichlo)romethyl-5-aryl(alkyl)-tetrazolo[1,5- a]pyrimidine through cyclocondensation of 1,1,1- trifluo(trichlo)ro-4-methoxy-3-alken-2-ones and 5- aminotetrazole, using ionic liquid.

Tetrazolopyrimidines are important biological agents with a wide range of pharmaceutical (e.g., hyperlipidemia, depression, glaucoma, and cardiac arrhythmias) and agrochemical uses. The synthesis of this class of compounds by cyclocondensation reaction requires extreme conditions such as the use of acids, high temperatures, and prolonged reaction times. Another drawback for obtaining these compounds is the low yields. Furthermore, the synthesis of trifluoromethylated tetrazolopyrimidine from trifluoromethylated substrates is very limited. The incorporation of fluorine into a drug allows simultaneous modulation of electronic, lipophilic, and steric parameters, all of which can critically influence both the pharmacodynamic and pharmacokinetic properties of drugs. In this work, we develop a simple and convenient protocol for the direct synthesis of 7- trifluo(trichlo)romethyl-5-aryl(alkyl)-tetrazolo[1,5- a]pyrimidine through cyclocondensation of 1,1,1- trifluo(trichlo)ro-4-methoxy-3-alken-2-ones and 5- aminotetrazole, using ionic liquid.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013819155310

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Como citar:

Scapin, Elisandra; Buriol, Lilian; Frizzo, Clarissa Piccinin; Martins, Marcos A. P.; "Synthesis of 7-trifluo[trichlo]romethyl-5-aryl[alkyl]-tetrazolo[1,5-a] pyrimidines in Ionic Liquid", p-176-176. 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_2013819155310