{"title":"Efficient on-water synthesis of novel pyrano[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines via catalyst-free one-pot three-component reaction","authors":"Fatemeh Hamidi Dastjerdi, Abbas Ali Esmaeili","doi":"10.1016/j.tet.2025.134559","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient, catalyst-free and eco-friendly synthesis of novel pyrano[3,2-<em>e</em>][1,2,4]triazolo[1,5-<em>a</em>]pyrimidines <em>via</em> cyclo-condensation of [1,2,4]triazolo[1,5-<em>a</em>]pyrimidine-5,7(4<em>H</em>,6<em>H</em>)-dione, aromatic aldehydes, and malononitrile has been described using ‘‘On-water” concept. The use of water as a clean media, catalyst-free conditions, excellent functional group acceptance, easier product isolation/purification without column chromatography, short reaction times, and good-to-excellent yields are the remarkable privileges of this protocol. Finally, <sup>1</sup>H, <sup>13</sup>C NMR, IR, mass spectra, and elemental analyses were conducted to determine the products’ structure.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134559"},"PeriodicalIF":2.1000,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025001152","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient, catalyst-free and eco-friendly synthesis of novel pyrano[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines via cyclo-condensation of [1,2,4]triazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione, aromatic aldehydes, and malononitrile has been described using ‘‘On-water” concept. The use of water as a clean media, catalyst-free conditions, excellent functional group acceptance, easier product isolation/purification without column chromatography, short reaction times, and good-to-excellent yields are the remarkable privileges of this protocol. Finally, 1H, 13C NMR, IR, mass spectra, and elemental analyses were conducted to determine the products’ structure.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.