AbstractAn efficient ligand-free cross-coupling reaction of 2-chloro-3-(chloromethyl)benzo[h]quinoline with N-heterocycles such as piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate using a catalytic amount of ZnO nanorods as a recyclable catalyst and KOH as the base in DMSO under reflux at 110°C is reported.

Mohana Roopan S

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Nawaz Khan F

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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Chemical Papers

A new and highly efficient microwave promoted N-alkylation of triazolo-quinazolinones was developed by treating various phenyl-substituted heterocyclic amines with benzyl chloride using K2CO3 as a base in the presence of DMF. Also the heterocyclic amines were synthesized by condensing the 3-amino-1,2,4-triazole substituted benzaldehydes and 1,3-cyclohexanedione in the presence of microwave irradiation under solvent free condition. The synthesized heterocycles 4a–o and 6a–o were further confirmed by using different spectroscopic techniques such as NMR and HRMS. The compounds 6a–o was studied for their solvatochromic property with increasing polarity of solvents. The determinations of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging effect of the scaffolds 6a–o were carried out by UV–Vis spectrometer. In terms of IC50 all the compounds have shown remarkable antioxidant property compared with Ascorbic acid. © 2016 Elsevier B.V.

Journal of Molecular Liquids

Conventional spectroscopic identification of N-alkylated triazolo-quinazolinones and its antioxidant, solvatochromism studies

The use of plant extract to synthesize nanoparticle has been considered as one of the eco-friendly method. Additionally, it is a strong alternate for conventional methods which includes chemical and physical approach. In this study, microwave assisted extraction of Carissa edulis (C. edulis) at 70 °C and 400 W was used to extract the secondary metabolites. Further, the metabolites were used as capping agent and Zn (NO3)2 as the metal precursor to synthesize ZnO nanoparticles (ZnO NPs). UV–Vis spectroscopy, FT-IR, XRD, SEM and HR-TEM were used for the characterization of nanoparticles. The Surface Plasmon Resonance around 358 nm from the UV–Vis spectroscopy result represents the ZnO NPs formation. The FT-IR confirms the presence of functional groups that acts as the capping agent for the synthesis of ZnO NPs. The crystalline structure of nanoparticles is revealed in the XRD result, morphology showed by SEM results and the size of the ZnO NPs were predicted by HR-TEM. We have carried out the photocatalytic degradation of Congo red at 365 nm in photo reactor using ZnO NPs. The result from the photocatalytic degradation Congo red showed rate constant is (− k) 0.4947 with 97{\%} of degradation. This is our first attempt on the C. edulis extract on ZnO NPs preparation and Congo red dye degradation revels that ZnO NPs exhibit good photocatalytic property.

Journal of Photochemistry and Photobiology B: Biology

Photocatalytic degradation of Congo red using Carissa edulis extract capped zinc oxide nanoparticles

In this paper, we have established for the first time, the terrific efficiency of aqueous extract of agricultural waste dried peel of sugar apple (Annona squamosa) in the rapid synthesis of stable SnO2 nanoparticles. In topical years, the deployment of secondary metabolites from plant extract has emerged as a novel technology for the synthesis of various nanoparticles. In this paper, we have studied the potential of SnO2 nanoparticles assembly using agricultural waste source for the first time. The synthesized nanoparticles were characterized and confirmed as SnO2 nanoparticles by using UV-visible spectroscopy, XRD, and TEM analysis. The motivation of this study was to examine cytotoxicity study of SnO2 nanoparticles against hepatocellular carcinoma cell line (HepG2). SnO2 nanoparticles inhibited the cell proliferation in a dose- and time-dependent manner with an IC50 value of 148 μg/mL. The treated cells showed an altered morphology with increasing concentrations of SnO2 nanoparticles. Our result shows that the SnO2 nanoparticles exhibit moderate cytotoxicity towards the hepatocellular carcinoma (HepG2) at tested concentrations.

Applied Biochemistry and Biotechnology

Biogenic-Production of SnO2 Nanoparticles and Its Cytotoxic Effect Against Hepatocellular Carcinoma Cell Line (HepG2)

The photochemical synthesis of a series of 2,3-dihydroquinazolin-4(1H)-ones were evaluated under the irradiation of visible light ({\textgreater}390 nm). The effect of the visible light mediated synthesis was carried out in the presence/absence of solvent. The effect of solvent plays a key role in the synthesis was evidenced through the formation of product in short duration. The solvatochromic effects of the fluorescent compounds (3a-k) were studied with respect to the solvents of increasing polarity (DCM {\textless} methanol {\textless} DMF {\textless} DMSO). The determination of in vitro anti-inflammatory activity of the compounds (3a-k) by the inhibition of bovine serum albumin (BSA) denaturation and 2,2-di(4-t-octylphenyl)-1-picrylhydrazyl (DOPPH•) radical scavenging consequence of the compounds (3a-k) were determined by spectroscopic technique. The compound 3j in DMSO exhibited extreme high quantum yield. The compound 3i was found to be superior both in the efficiency of the anti-inflammatory activity and radical scavenging ability.

2,3-Dihydroquinazolin-4(1H)-ones: Visible light mediated synthesis, solvatochromism and biological activity

A series of 9-substituted 1,8-dioxo-octahydroxanthenes, 3a-k were synthesized and evaluated for their anti-tubercular and in vitro anti-inflammatory potential. Compounds 3b, 3d, 3e, 3f, 3g, and 3k demonstrated their potential anti-tubercular activity at 0.4 lg/ml comparable to streptomycin and pyrazinamide (standard drugs) screened by Microplate Alamar Blue assay against Mycobacterium tuberculosis H37 Ra. Compounds 3j, 3e, 3f, and 3c showed good in vitro anti-inflammatory activity by the inhibition of enzyme MMP-2 75, 65, 70, and 60 % and inhibition of enzyme MMP-9 by 90, 70, 60, and 60 %, respectively by gelatin zymography on gel electrophoresis. Standard drug tetracycline (300 lg/ml) is used as positive control which showed 90 % inhibition. The percentage inhibition was determined by a gel documentation system. DMSO was used as solvent control which did not show any inhibition. © Springer Science+Business Media New York 2014.

Medicinal Chemistry Research

Potential anti-tubercular and in vitro anti-inflammatory agents: 9-substituted 1,8-dioxo-octahydroxanthenes through cascade/domino reaction by citric fruit juices

An efficient and regioselective N-alkylation of 4(3H)-pyrimidone with various electrophiles in the presence of Fe nano particle is reported. The catalyst initiates N-alkylation of amides by alkyl chlorides. The reaction of equimolar 4(3H)-pyrimidone and 2-chloro-3-(chloromethyl)quinolines in the presence of KOH and Fe nano particle (5 mol %) in DMSO solution under reflux condition formed 3-[(2-chloroquinolin-3-yl]methyl)pyrimidin-4(3H)ones. © 2010 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Fe nano particles mediated C–N bond-forming reaction: Regioselective synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3H)ones

In the title compound, C18H13Cl2NO2, the quinoline ring system is almost planar (r.m.s. deviation 0.009 Å), and the phenyl and carboxyl-ate planes are twisted away from it by 59.2 (1) and 65.9 (2)°, respectively.

Fulltext

Acta Crystallographica Section E Structure Reports Online

Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate

The quinolinyl fused-ring of the title compound, C11H 8ClNO, is almost planar (r.m.s. deviation = 0.013 Å); the formyl group is slightly bent out of the plane of the fused ring system [C- C- C- O torsion angle = 13.5 (4)°].

2-Chloro-6-methylquinoline-3-carbaldehyde

The quinolinyl fused ring system of the title compound, C 10H6ClNO, is planar (r.m.s. deviation = 0.018 Å); the formyl group is slightly bent out of the plane of the fused ring system [C- C- C- O torsion angle = 8.2 (3)°].

2-Chloroquinoline-3-carbaldehyde

The benzo[h]quinolinyl fused-ring of the title compound, C 14H8ClNO, is planar (r.m.s. deviation = 0.016 Å); the formyl group is slightly bent out of the plane [the C- C- C- O torsion angle is 10.7 (4)°].

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ISSN	03666352
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