Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles
作者:Zaira Monasterio、Aitziber Irastorza、José I. Miranda、Jesus M. Aizpurua
DOI:10.1021/acs.orglett.6b01177
日期:2016.5.20
carrying latent “click” functionality, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides an efficient route to 1,5-disubstituted 1,2,3-triazoles. The azide and alkyne groups incorporated by N-alkylation can be submitted to further copper-catalyzed azide–alkyne and Huisgen cycloadditions to provide bis(1,2,3-triazoles)
1-(新戊酰氧基甲基)-1,2,3-三唑与带有潜在“喀哒”官能团的烷基三氟甲磺酸酯的N3-烷基化,然后由亲核试剂促进所得的强亲电中间体三唑鎓盐的N1-去烷基化,提供了一条有效的途径1,5-二取代的1,2,3-三唑。通过N-烷基化结合的叠氮化物和炔基可进一步用于铜催化的叠氮化物-炔烃和Huisgen环加成反应,以提供具有前所未有的1,5 / 1,4取代模式的双(1,2,3-三唑)。