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Issue 40, 2017
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A convenient synthesis of 1-aryl-1H-1,2,3-triazoles from aliphatic substrates

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Abstract

A convenient synthesis of 1-aryl-1H-1,2,3-triazoles through the one pot cascade reactions of alkynes with aliphatic azides and allenic ketones is presented. Mechanically, the formation of the title compounds involves a copper-catalyzed cycloaddition of alkyne with 4-azido-3-oxobutanoate to give 3-oxo-4-(1H-1,2,3-triazol-1-yl)butanoate as a key intermediate followed by its [3 + 3] annulation with allenic ketone through Michael addition and intramolecular condensation. A comparison study showed that using aliphatic azide as the substrate is superior to aromatic azide in terms of efficiency and selectivity. Furthermore, the 1-aryl-1H-1,2,3-triazoles bearing a 2′-bromophenyl unit attached on the 2-position of the in situ formed aryl ring obtained herein could be readily transformed into the biologically and pharmaceutically valuable tretracyclic triazolophenanthridines with good yields via a Pd-catalyzed C–H arylation.

Graphical abstract: A convenient synthesis of 1-aryl-1H-1,2,3-triazoles from aliphatic substrates

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Publication details

The article was received on 16 Aug 2017, accepted on 22 Sep 2017 and first published on 22 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02035J
Citation: Org. Biomol. Chem., 2017,15, 8529-8534
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    A convenient synthesis of 1-aryl-1H-1,2,3-triazoles from aliphatic substrates

    Q. Wang, X. Shi, X. Zhang and X. Fan, Org. Biomol. Chem., 2017, 15, 8529
    DOI: 10.1039/C7OB02035J

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