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Synthesis of fluorescent heterocycles via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

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Abstract

A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.

Graphical abstract: Synthesis of fluorescent heterocycles via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

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Publication details

The article was received on 03 Jun 2017, accepted on 30 Jun 2017 and first published on 30 Jun 2017


Article type: Communication
DOI: 10.1039/C7OB01239J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of fluorescent heterocycles via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

    G. Martinez-Ariza, B. T. Mehari, L. A. G. Pinho, C. Foley, K. Day, J. C. Jewett and C. Hulme, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01239J

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