Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

One-Step Synthesis of Novel Heterocycles of Dihydroquinolone-Coumarin in the Presence of ZnBr2 Catalyst

Document Type : Research Article

Authors
Mostafa Kiamehr 1
Leyla Mohammadkhani 1
Reza Safari 1
Behzad Jafari 2
Peter Langer 2
1 Department of Chemistry, Faculty of Science, University of Qom, Ghadir Blvd, Qom, I.R. IRAN
2 Institut für Chemie der Universität Rostock, Albert-Einstein-Straße 3a, D-18059 Rostock, GERMANY
Abstract
In view of the biological and pharmaceutical significance of coumarin and 3,4-dihydroquinolone structures, such as anticancer, anticoagulation of blood vessels and anti-HIV activities, and advantageous of synthesis of hybrid molecules by the combination of known pharmacophores for the development of a diverse range of novel pharmaceutical agents as potent drugs with many improved properties, in this article, various novel tetra- and pentacyclic heterocycles of 3,4-dihydroquinolones annulated tetrahydropyranocoumarin and α-pyrone were synthesized via domino Knoevenagel hetero Diels-Alder reaction of N-acrylated anthranilaldehyde with 4-hydroxy-coumarin and α-pyrone (4-hydroxy-6-methyl-2H-pyran-2-one) in the presence of 50 mol% ZnBr2 as a mild and low cost catalyst in refluxing acetic acid in one step. All products achieved with high yields with excellent regioselectivity and stereoselectivity.
Keywords
ZnBr2 catalyst
Coumarin
3,4-Dihydroquinolone
Hetero Diels-Alder reaction

Subjects

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