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Issue 18, 2018
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One-pot synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin and effective cyclization to unexpected 3,4-dihydropyridines

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Abstract

A facile synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin, aldehydes and cyclic-ketones via a one-pot aldol condensation and subsequent Michael addition reaction in the presence of a single catalyst of L-proline under mild reaction conditions has been developed. Novel 1,5-diketones were further cyclized to unexpected 3,4-dihydropyridines rather than generally formed pyridine analogues with ammonium acetate in acetic acid. One pot, high yields (72–92%) for novel 1,5-diketones and (70–90%) for the 3,4-dihydropyridine adducts, easy work-up and purification of products are the key advantages of this method.

Graphical abstract: One-pot synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin and effective cyclization to unexpected 3,4-dihydropyridines

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Publication details

The article was received on 24 Mar 2018, accepted on 11 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00718G
Citation: Org. Biomol. Chem., 2018,16, 3428-3437
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    One-pot synthesis of 1,5-diketones from 3-acetyl-4-hydroxycoumarin and effective cyclization to unexpected 3,4-dihydropyridines

    M. Waheed, N. Ahmed, M. A. Alsharif, M. I. Alahmdi and S. Mukhtar, Org. Biomol. Chem., 2018, 16, 3428
    DOI: 10.1039/C8OB00718G

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