Literature DB >> 24394386

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

Clarissa P Frizzo1, Elisandra Scapin1, Mara R B Marzari1, Taiana S München1, Nilo Zanatta1, Helio G Bonacorso1, Lilian Buriol2, Marcos A P Martins3.   

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).
Copyright © 2013 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  1,2,4-Triazolo[1,5-a]pyrimidine; Enaminones; Trifluoromethyl enones; Ultrasound

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Year:  2013        PMID: 24394386     DOI: 10.1016/j.ultsonch.2013.12.007

Source DB:  PubMed          Journal:  Ultrason Sonochem        ISSN: 1350-4177            Impact factor:   7.491


  2 in total

1.  Design, Synthesis, and Evaluation of Anticonvulsant Activities of New Triazolopyrimidine Derivatives.

Authors:  Mingxia Song; Wennan Zhao; Yangnv Zhu; Wenli Liu; Xianqing Deng; Yushan Huang
Journal:  Front Chem       Date:  2022-06-23       Impact factor: 5.545

2.  Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines.

Authors:  Elisandra Scapin; Paulo R S Salbego; Caroline R Bender; Alexandre R Meyer; Anderson B Pagliari; Tainára Orlando; Geórgia C Zimmer; Clarissa P Frizzo; Helio G Bonacorso; Nilo Zanatta; Marcos A P Martins
Journal:  Beilstein J Org Chem       Date:  2017-11-10       Impact factor: 2.883

  2 in total

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