The ultrasound-promoted synthesis of novel bipodal and tripodalpiperidin-4- ones was carried out by the reaction of 4-piperidone hydrochloride monohydrate with different alkylating and acylating agents. It was preferably reduced to respective piperidin-4-ols by ultrasonic irradiation using silica chloride, which maintains higher yields by acting as an effective supporting polymer. The sterically hindered phthaloyl derivative of piperidin-4-one was synthesized by ultrasonic irradiation which was difficult by conventional methods. © 2011 Elsevier B.V. All rights reserved.

Vijayakumar V

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Rajesh K

Palakshi Reddy B

Fulltext

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VIT University

Ultrasonics Sonochemistry

AbstractThe crystal structure analysis of a 2,6-diaryl 4-piperidone derivative, isolated as a mono-methanol solvate, reveals that both the piperidone and the methanol molecule lie on a crystallographic mirror plane. A chair conformation is found for the piperidone ring with the aryl and methyl groups in equatorial positions. The most prominent feature of the molecular packing is the formation of supramolecular zigzag chains mediated by amine-N–H···O(methanol) and hydroxyl-O–H···N(amine) hydrogen bonds, i.e. the methanol molecule serves as a bridge between piperidone molecules. The molecular structure is compared with that determined in an unsolvated form and the gas-phase equilibrium structure, obtained using density-functional theory (DFT); differences relate, in the main, to the relative dispositions of the aryl rings. An analysis of the Hirshfeld surfaces of the experimental structures indicates very similar relative contributions with the notable exception being the contribution by O···H/H···O which at 13.7% in the methanol solvate is &gt;8.5% in the unsolvated form.

Zeitschrift für Kristallographie - Crystalline Materials

Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate

Abstract A new series of piperidine derivatives namely 3,5-dimethyl-2,6-diaryl-1-propionyl-piperidin-4-ones were synthesized. The structure of the compound, 3, 5-dimethyl-2,6-phenyl-1-propionyl-piperidin-4-one was determined unambiguously using NMR, IR and single crystal X-ray diffraction techniques. DFT and its time dependent version based calculations have been carried out to analyze its ground state electronic structure and to interpret the experimental spectroscopic data. The current study also explores into the spectroscopic property of these piperidine-4-one compounds and proposes these molecules as potential sunscreens and UV filters. © 2015 Elsevier B.V.

Journal of Molecular Structure

Synthesis, spectral characterization and DFT analysis for the validation of 2, 6 diaryl -piperidin-4-ones as potential sunscreens and UV filters

Bi-, tri- and tetrapodal polyhydroquinolines and 1,4-dihydropyridines were synthesised by the reaction of various alkylating agents with polyhydroquinolines and 1,4-dihydropyridines under sonication conditions. These were in turn converted to the corresponding pyridines also using sonication. Sonication produced higher yields in a faster reaction time. All the synthesized compounds were characterized using spectral data. © 2014 The Royal Society of Chemistry.

RSC Adv.

Ultrasound-promoted synthesis of bi-, tri- and tetrapodal polyhydroquinolines, 1,4-dihydropyridines and the corresponding pyridines

A series of quinoline-based coumarin derivatives have been synthesized by one pot dehydrochlorination of 2,4-dichloroquinolines (1a-g); 7-hydroxy-4-methyl-2H-chromen-2-one (2) under ultrasonic irradiation method with high regio selectivity. All the synthesized compounds were characterized through spectral data and screened against representative antibacterial and antioxidant activities. Some of the compounds are found to be equipotent or more potent than that of standard drugs. Molecular docking studies show that the binding energy value of the compounds is very less than that of standard chloroquine and amodiaquine drugs. © 2012 Springer Science+Business Media New York.

Medicinal Chemistry Research

Ultrasound-promoted synthesis, biological evaluation and molecular docking of novel 7-(2-chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-one derivatives

Ultrasound-promoted reaction of substituted 2,4-dichloroquinolines (1) with ethyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5- carboxylate (2) in the presence of K2CO3 as mild base at moderate temperatures leads to 2-chloroquinolin-4-pyrimidine carboxylate derivatives (3) with high regioselectivity. All the compounds synthesized were characterized by use of spectral data and screened for their antibacterial activity against two Gram-positive (Staphylococcus aureus, Bacillus cereus) and two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. Activity was moderate. © 2012 Springer Science+Business Media B.V.

Research on Chemical Intermediates

Ultrasound-promoted synthesis of novel 2-chloroquinolin-4-pyrimidine carboxylate derivatives as potential antibacterial agents

In the mol-ecule of the title compound, C18H24N 2O2, the piperidine rings are in chair conformations. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonding. There are neither C-H⋯π nor π-π inter-actions in the structure.

Acta Crystallographica Section E Structure Reports Online

1,1′-(p-Phenylenedimethylene)dipiperidin-4-one

In the structure of the title compound, C27H39N 3O3, each of the (4-oxopiperidin-1-yl)methyl residues adopts a flattened chair conformation (with the N and carbonyl groups being oriented to either side of the central C4 plane) and they occupy positions approximately orthogonal to the central benzene ring [Cbenzene - C - Cmethyl-ene - N torsion angles 103.4 (2), -104.4 (3) and 71.9 (3)°]; further, two of these residues are oriented to one side of the central benzene ring with the third to the other side. In the crystal packing, supra-molecular layers in the ab plane are sustained by C - H⋯O inter-actions.

1-[2,4,6-Trimethyl-3,5-bis(4-oxopiperidin-1-ylmethyl)benzyl]piperidin-4-one

Organic Reactions

The Dieckmann Condensation (Including the Thorpe-Ziegler Condensation)

Recueil des Travaux Chimiques des Pays-Bas

Synthesis and exploratory photophysical investigation of donor-bridge-acceptor systems derived from N-substituted 4-piperidones

Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles

Ultrasound-promoted synthesis of novel bipodal and tripodalpiperidin-4-ones and silica chloride mediated conversion to its piperidin-4-ols: Synthesis and structural confinements

Journal	Data powered by TypesetUltrasonics Sonochemistry
Publisher	Data powered by TypesetElsevier BV
ISSN	1350-4177
Open Access	0