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

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 f...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-05, Vol.16 (18), p.3428-3437
Main Authors: Waheed, Mohd, Ahmed, Naseem, Alsharif, Meshari A, Alahmdi, Mohammed Issa, Mukhtar, Sayeed
Format: Article
Language:English
Subjects:
Acetic acid
Adducts
Aldehydes
Ammonium
Ammonium acetate
Condensates
Dihydropyridine
Diketones
Ketones
L-Proline
Michael reaction
Proline
Purification
Pyridines
Synthesis
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Summary: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. A one-pot synthesis of new 4-hydroxycoumarin-based 1,5-diketones and effective cyclization to quite stable and unexpected 3,4-dihydropyridines has been developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00718g