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Abstract An efficient green method for the synthesis of Coumarins acts as urease inhibitors [10], corrosion
oxazino quinoline-2-amine derivatives, oxazino quinoline inhibitors [11], optical brighteners [12], dispersed
derivatives and chromeno oxazin-5-one derivatives have fluorescent and laser dyes [13] used in Dye Sensitized
been synthesized through cyclization of aromatic Solar Cells (DSSCs)[14-21]. The main importance lies in
aldehyde, ammonium acetate, substituted amides and 8- the functionally substituted chromenes in the field of
hydroxy-quinoline or 4-hydroxy coumarin by one-pot medicinal chemistry [22-23] as natural fruit and plant
condensation method is described. The synthesized extract in Ammi Visnaga as visnadine [25] and in
compounds are characterized by FT-IR, 1H NMR and Phlojodicarpus sibiricus as Khellactone [26]. These have
MASS spectral techniques and are screened further for perfect vasodilatory properties.
biological activities against Escherichia coli, Chromene is the privileged structural component for
Pseudomonas aeruginosa, Staphylococcus aureus and various natural products consisting of photochemical
Bacillus subtilis using cup plate method and disc diffusion properties. It is the backbone of many polyphenols found
method. mostly in alkaloids, flavanoids, tocopherols and
Keywords One-pot Synthesis, Biological activity, anthocyanins [27]. The chromene derivatives are
Chromeno oxazin-5-one derivatives, Oxazino quinoline- potential anticancer agents [28]. Earlier several methods
2-amine derivatives and Oxazino quinoline derivative. are reported for the synthesis of oxazino quinolines, from
aromatic aldehydes, 6-quinolinol and urea under solvent-
I. INTRODUCTION free conditions using p-toluene sulfonic acid at 150
One pot synthesis through multi-component reactions C [6], 6-quinolinol, benzaldehyde and methylcarbamate
[MCRs] has a great role in organic synthesis. These are using H2O/ Triethylbenzylammonium- chloride using
one step reactions, where the reactants are subjected into water as solvent [29] and quinoline, dimethyl
a single reactor to form a desired product with high yields acetylenedicarboxylate zwitterions and aldehydes using
without any intermediate formation. Its importance lies toluene as solvent [30], 8-hydroxyquinoline, thiourea and
mainly in the synthesis of medicinally potent compounds formaldehyde by condensation method using N, N-
and its convenient preparation than the conventional Dimethylformamide medium as solvent [31].
methods, thereby having great advantage over convergent In this a novel preparation of oxazino quinolines using
and conventional synthesis [1-3]. different reactants is reported. The main objective of our
The compounds consisting of quinoline moiety have research is synthesis of active heterocyclic compounds,
broad range of applications with biological activity such which involves greener procedures, shorter reaction
as anti-malarial, anti-asthmatic, anti-inflammatory and times, lower temperature conditions, higher yields, and
anti-bacterial properties [4,5]. On the other hand, economically desirable processes.
oxazinone derivatives have a considerable property as a Now we report an efficient greener synthesis of oxazino
non-nucleoside reverse transcriptase inhibitor to fight quinoline-2-amine derivatives, oxazino quinoline
against HIV virus which is approved by FDA [6]. derivatives and chromeno oxazin-5-one derivatives
Heterocyclic compounds having coumarin nuclei have through cyclization of aromatic aldehyde, ammonium
aroused wide range of biological activities [7, 8] such as acetate, amide and 8-hydroxy quinoline ("Fig.1") or 4-
antibacterial, anticoagulant, antiviral, antifungal, hydroxy coumarin ("Fig.2") through one pot condensation
anticancer and anti-inflammatory properties [9]. method without catalyst.
(1)
ACKNOWLEDGEMENTS
The authors wish to thank UGC for the facilities provided
X
H2N X H2N X
through UGC-MRP No. F.41-371/2012 to SPD, UGC-FIP
O
NH OH
H N
-NH3 O to YVK and MS and DST-Advanced Analytical
N N N
Laboratory, Andhra University, Visakhapatnam for the
(1) characterization facilities provided for the work.
Fig.3: Plausible mechanism for the synthesis of oxazino
quinoline-2- amine and oxazino quinoline derivatives REFERENCES
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