An efficient and regioselective O-alkylation of amides with a variety of electrophiles in the presence of silver nanoparticles is reported as part of our recent research on building blocks for synthesis of natural products. The nano-silver catalyst initiates O-alkylation of the amides by heteroalkyl halides. Reaction of equimolar 3-acetyl-6-chloro-4-phenylquinolin-2(1H)-one and 2-chloro-3-(chloro-methyl)quinolines in the presence of silver nanoparticles in DMSO solution under reflux condition leads to the formation of 1-{1-[2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones. © Springer Science+Business Media B.V. 2011.

Mohana Roopan S

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Nawaz Khan F

Kumar R

Computer Science

School of Computer Science and Engineering

Chennai Campus

Gund M

Jin J.S

Kumar A.S.

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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VIT University

Research on Chemical Intermediates

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

A series of 6,7-dihydro-[1,2,4]triazolo[5,1-b]quinazolin-8(5H)-ones, 4a–o were synthesized via a one-pot, multicomponent reaction in the presence of water as a solvent under microwave irradiation using ceric ammonium nitrate as an oxidizing agent. This techno-chemical method provides a rapid construction of higher molecules in short duration with high yield. The adopted method was carried out in the presence of water without catalyst and yielded the compounds without any side products, and thus further purification of compounds by column chromatography was not required. All the synthesized compounds, 4a–o were screened for their 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity. All the compounds, 4a–o possessed moderate antioxidant activity when compared to their standard antioxidant (ascorbic acid). © 2015, Springer Science+Business Media Dordrecht.

Microwave assisted synthesis of ring junction heterocyclic antioxidants

Heterocyclic motif is an important scaffold which has both industrial and pharmaceutical applications. These motifs can be prepared using wide variety of reaction conditions such as the use of expensive catalyst, toxic solvent, harsh reaction condition like the use of base, high temperature, and multistep reaction. Although various methods are involved, the chemistry arena is now shifted towards the greener way of synthesis. Nanocatalyst constitutes an important role in the green synthesis. This is because the activity of the catalyst resides in the exposed portion of the particles. By decreasing the size of the catalyst, advantages such as more surface area would be exposed to the reactant, only negligible amount would be required to give the significant result and selectivity could be achieved, thereby, eliminating the undesired products. The current review enlists the various types of nanocatalyst involved in the heterocyclic ring formation and also some other important functionalization over the ring.

Fulltext

Journal of Nanomaterials

Function of Nanocatalyst in Chemistry of Organic Compounds Revolution: An Overview

An efficient and simple thiourea-mediated regioselective synthesis of symmetrical and unsymmetrical diversified thioethers is reported. The regioselective reaction avoids byproduct formation and offers simplified methodology, wider applicability, and easy workability and an environmentally friendly approach toward symmetrical and unsymmetrical thioethers. The mechanism of formation of thiols and symmetrical and unsymmetrical thioethers involving a sulfur surrogate is described. © 2014 American Chemical Society.

Industrial & Engineering Chemistry Research

Thiourea-Mediated Regioselective Synthesis of Symmetrical and Unsymmetrical Diversified Thioethers

A facile and microwave accelerated reaction of 1-chloro-3-(4-chlorophenyl) isoquinoline with various heterocyclic amines, catalyzed by Pd, in the presence of BINAP additive and sodium carbonate as the base, leads to the formation of 3-(4-chlorophenyl)-1-(1H-1,2,3-triazol-1-yl)isoquinoline, 3-(4-chlorophenyl)-1- (1H-imidazol-1-yl)isoquinoline and 3-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl) isoquinoline via Buchwald protocol in good yields. Similarly pyrazolylisoquinolines are also reported. © 2010 Elsevier Ltd.

Tetrahedron Letters

An effective BINAP and microwave accelerated palladium-catalyzed amination of 1-chloroisoquinolines in the synthesis of new 1,3-disubstituted isoquinolines

In the title molecule, C23H14N4, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.038 (2) Å and a maximum deviation of -0.030 (2) Å from the mean plane of the triazole ring C atom which is bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.65 (8) and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, molecules are linked by weak aromatic π-π interactions [centroid-centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical intermolecular C - H⋯N hydrogen bond. © 2010.

Acta Crystallographica Section E Structure Reports Online

4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

In the title molecule, C22H14ClN 3, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of 0.062 (1) Å for the triazole ring C atom, bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.02 (6) and 62.16 (6)°, respectively, to the mean plane of the triazoloisoquinoline ring system. The molecule is stabilized by a weak intramolecular π-π inter-action [centroid-centroid distance = 3.7089 (10) Å] between the benzene and phenyl rings. In the crystal structure, weak intermolecular C - H⋯N hydrogen bonds and C - H⋯π interactions link the molecules. © 2010.

3-(4-Chlorophenyl)-5-phenyl-1,2,4-triazolo[3,4-a]isoquinoline

In the title compound, C16H13ClN2O, the quinoline ring system is essentially planar, with a maximum deviation of 0.021 (2) Å. The pyridone ring is oriented at a dihedral angle of 85.93 (6)° with respect to the quinoline ring system. In the crystal structure, inter-molecular C - H⋯O hydrogen bonds link the mol-ecules along the b axis. Weak π-π stacking inter-actions [centroid-centroid distances = 3.7218 (9) and 3.6083 (9) Å] are also observed.

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ISSN	0922-6168
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