Ultrasound irradiation promotes the synthesis of new 1,2,4-triazolo[1,5-a]pyrimidine

•A series of 7-trifluoromethyl[aryl]-triazolo[1,5-a]pyrimidines under ultrasound irradiation was synthesized.•Ultrasound irradiation method was more efficient than conventional thermal heating.•Products were obtained with excellent yields. Ultrasonic irradiation was used in the synthesis of a series...

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Bibliographic Details
Published in:Ultrasonics sonochemistry 2014-05, Vol.21 (3), p.958-962
Main Authors: Frizzo, Clarissa P., Scapin, Elisandra, Marzari, Mara R.B., München, Taiana S., Zanatta, Nilo, Bonacorso, Helio G., Buriol, Lilian, Martins, Marcos A.P.
Format: Article
Language:English
Subjects:
1,2,4-Triazolo[1,5-a]pyrimidine
Chemistry
Chemistry Techniques, Synthetic
Enaminones
Exact sciences and technology
General and physical chemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
Trifluoromethyl enones
Ultrasonic chemistry
Ultrasonics
Ultrasound
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Summary:•A series of 7-trifluoromethyl[aryl]-triazolo[1,5-a]pyrimidines under ultrasound irradiation was synthesized.•Ultrasound irradiation method was more efficient than conventional thermal heating.•Products were obtained with excellent yields. Ultrasonic irradiation was used in the synthesis of a series of novel 1,2,4-triazolo[1,5-a]pyrimidines. The products were synthetized from the cyclocondensation reaction of 1,1,1-trifluoro-4-metoxy-3-alken-2-one [CF3C(O)CHC(R)OMe, where R=Ph, 4-F-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH3-C6H4, 4-CH3O-C6H4, Thien-2-yl, Biphen-4-yl] or β-enaminones [RC(O)CHCHNMe2, where R=Ph, 4-F-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH3-C6H4, 4-CH3O-C6H4, 4-NO2-C6H4, Thien-2-yl, Biphen-4-yl, Naphth-2-yl, Pyrrol-2-yl, CCl3] with 5-amino-1,2,4-triazole in acetic acid at 99°C with 5–17min of ultrasound irradiation. This methodology has shown several advantages, such as shorter reaction times, mild conditions, high regioselectivity, and excellent yields, when compared with conventional thermal heating (oil bath).
ISSN:1350-4177
1873-2828
DOI:10.1016/j.ultsonch.2013.12.007