Journal of Chemistry and Biochemistry
December 2016, Vol. 4, No. 2, pp. 45-59
ISSN 2374-2712 (Print) 2374-2720 (Online)
Copyright © The Author(s). 2015. All Rights Reserved.
Published by American Research Institute for Policy Development
DOI: 10.15640/jcb.v4n2a5
URL: https://doi.org/10.15640/jcb.v4n2a5
Synthesis of Some Novel Derivatives of Substituted 2H-[1]-
Benzopyran-2-Ones and Their Antimicrobial Activity
Ramiz HOTI
1
, Naser Troni
2
*, Idriz VEHAPI
3
, GJyle MULLIQI-OSMANI
4
,
Hamit ISMAILI
5
& Veprim THAÇI
6
Abstract
Novel derivatives of substituted bezopyran-2-ones are synthesized by catalytic reactions
under refluxing conditions. 4-Hydrazinyl-3-nitrobenzopyran-2-one 4 is synthesized from
4-hydroxybenzopyran-2-one 1 via three steps reaction. By condensation reaction of 4-
hydrazinyl-3-nitrobenzopyran-2-one 4 and aromatic aldehydes, corresponding 4-(N-
benzylidene-hydrazino)-3-nitrobenzopyran-2-ones 5(a-c) are obtained. Cyclization
reaction of 4-hydroxybenzopyran-2-one 1 with aromatic aldehydes and malononitrile, in
the presence of SDS, resulted by formation of 2-amino-5-oxo-4-phenyl-(4H, 5H)
pyrano-[3,2-c]-chromen-3-carbonitrile derivatives 6(a-c) , whereas by reacting of 4-
hydroxybenzopyran-2-one 1 and aromatic aldehydes, in presence of SDS, corresponding
3,3’-(benzylidene)-bis-4-hydroxyibenzopyran-2-ones 7(a-c) are synthesized. The
synthesized products are characterized on the basis of spectrometric data. Antimicrobial
activity of products 5(a-c), 6(a-c) and 7(a-c) against S. aurous , E . coli and Klebsiella are
investigated measuring of inhibition zones around the discs which are marked with their
N, N-DMF solutions. Compounds of series 5 and 6 showed considerable antimicrobial
activity against these microorganisms, whereas compounds of series 7 showed moderate
activity. Impact of the substituents in antimicrobial activity also is investigated.
Keywords: Benzopyran-2-one; benzaldehyde condensation; cyclization; antibacterial
activity
1
Faculty of Nature Sciences, Department of Chemistry, University of Prishtina, “Mother Teresa” street, 10000
Prishtina, Kosovo.
2
Faculty of Nature Sciences, Department of Chemistry, University of Prishtina, “Mother Teresa” street, 10000
Prishtina, Kosovo. E-mail: naser_troni@ yahoo.com; ramizhoti@ yahoo.com; Phone: + 381 (0)38 249 872; Fax:
+381 (0)38 226 104
3
Faculty of Nature Sciences, Department of Biology, University of Prishtina, “Mother Teresa” street, 10000
Prishtina, Kosovo.
4
Institute of Public Health of Kosovo,“Rrethi i Spitalit” street, 10000 Prishtina, Kosovo
5
Faculty of Nature Sciences, Department of Chemistry, University of Prishtina, “Mother Teresa” street, 10000
Prishtina, Kosovo.
6
Faculty of Nature Sciences, Department of Chemistry, University of Prishtina, “Mother Teresa” street, 10000
Prishtina, Kosovo.