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Issue 23, 2018
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Copper-catalyzed [3 + 2 + 1] annulation for functionalized pyridines as potent and dynamic UV absorbers

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Abstract

A novel Cu(OTf)2-catalyzed [3 + 2 + 1] annulation of chromenone carbaldehydes or benzochromenone carbaldehydes with β-enamino substrates and ammonium acetate is developed. This protocol provides a facile and efficient one-pot procedure for the construction of diverse and functionalized pyridines bearing a variety of substituents. This [3 + 2 + 1] annulation proceeds via a cascade aldol-type reaction, deprotonation and protonation, Michael addition and ring opening, and intramolecular Michael addition and heteroaromatization. The synthesized compounds exhibited potent and dynamic UV absorption for broad spectrum coverage.

Graphical abstract: Copper-catalyzed [3 + 2 + 1] annulation for functionalized pyridines as potent and dynamic UV absorbers

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Publication details

The article was received on 28 Jul 2018, accepted on 08 Sep 2018 and first published on 10 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00782A
Citation: Org. Chem. Front., 2018,5, 3368-3373

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    Copper-catalyzed [3 + 2 + 1] annulation for functionalized pyridines as potent and dynamic UV absorbers

    S. M. B. Maezono, S. H. Kim and Y. R. Lee, Org. Chem. Front., 2018, 5, 3368
    DOI: 10.1039/C8QO00782A

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