Cu(I)-catalyzed alkyne–azide ‘click’ cycloaddition (CuAAC): a clean, efficient, and mild synthesis of new 1,4-disubstituted 1H-1,2,3-triazole-linked 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile–crystal structure View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-04

AUTHORS

Khadijeh Ojaghi Aghbash, Nader Noroozi Pesyan, Ertan Şahin

ABSTRACT

Cu(I)-catalyzed alkyne–azide ‘click’ cycloaddition (CuAAC) is an important ‘‘click chemistry’’ reaction that is widely known in materials science, chemical biology, and pharmaceutical chemistry. The CuAAC reaction of terminal alkynes affords an efficient and mild production of triazolic 1,4-disubstituted compounds. In this work, a green and valuable method was introduced for the synthesis of the category of different new 1,4-disubstituted 1,2,3-triazole swapped with a 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano moiety. These triazolic derivatives were produced by treatment of various 2-amino-6-(azidomethyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles with phenylacetylene in the presence of CuI as a catalyst with excellent yields (because CuAAC is selective to 1,4-disubstituted triazole derivatives) in a green solvent (ethanol/water). All structures were evaluated by 13C, 1H NMR, and FT-IR spectroscopy and a compound was analyzed by crystallography (X-ray) technique. More... »

PAGES

2079-2094

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11164-018-03723-x

DOI

http://dx.doi.org/10.1007/s11164-018-03723-x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1111328169


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