title: Ultrasound irradiation promotes the synthesis of new 1,2,4-triazolo[1,5-a]pyrimidine.
abstract: 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 5-17 min 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).
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Clarissa P
authors.initials: CP
authors.lastname: Frizzo
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Elisandra
authors.initials: E
authors.lastname: Scapin
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Mara R B
authors.initials: MR
authors.lastname: Marzari
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Taiana S
authors.initials: TS
authors.lastname: München
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Nilo
authors.initials: N
authors.lastname: Zanatta
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil.
authors.forename: Helio G
authors.initials: HG
authors.lastname: Bonacorso
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil. Electronic address: liburiol@yahoo.com.br.
authors.forename: Lilian
authors.initials: L
authors.lastname: Buriol
authors.affiliation: Núcleo de Química de Heterociclos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil. Electronic address: mmartins@base.ufsm.br.
authors.forename: Marcos A P
authors.initials: MA
authors.lastname: Martins
mesh_terms: D060326:Chemistry Techniques, Synthetic; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014465:Ultrasonics
chemical_list: C419143:1,2,4-triazole(1,5a)pyrimidine; D011743:Pyrimidines; D014230:Triazoles
keywords: 1,2,4-Triazolo[1,5-a]pyrimidine; Enaminones; Trifluoromethyl enones; Ultrasound