Synthesis and crystal structures of 2-methyl-4-aryl-5-oxo-5H-indeno [1,2-b] pyridine carboxylate derivatives

doi:10.1186/1752-153X-8-34

Paper

Synthesis and crystal structures of 2-methyl-4-aryl-5-oxo-5H-indeno [1,2-b] pyridine carboxylate derivatives

Published May 29, 2014 · R. Pandian, Edayadulla Naushad, V. Vijayakumar

Chemistry Central Journal

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6

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Abstract

BackgroundHantzsch 1,4-dihydropyridines (Hantzsch1,4-DHP) have been extensively utilized as the analogs of nicotinamide adenine dinucleotide (NADH) coenzyme to study the mechanism and various redox processes. During the redox processes 1,4-DHP systems undergo transformation into the corresponding pyridine derivatives through oxidation. Consequently, the interest in this aromatization reaction, investigation of a wide range of 1, 4-DHPs continues to attract the attention of researchers. Herein, we report the preparation of pyridine derivatives and the crystal structures determined by X-ray crystallographic methods.ResultsThe crystal structures and conformational studies of two organic compounds, namely ethyl 2-methyl-4-phenyl-5-oxo-5H-indeno [1,2-b] pyridine-3-carboxylate (I) and ethyl 2-methyl-4-(4 chlorophenyl)-5-oxo-5H-indeno [1,2-b] pyridine-3-carboxylate (II) are reported. The terminal ethyl group of the compound I is disordered over two positions with the refined occupancies of 0.645 & 0.355 and C8 one dimensional zig-zag chain running along 101 direction through C-H…O type of intermolecular interactions. In the compound II, C-H…O interactions connect the molecules to form an R22 (16) dimer running along 011 direction.ConclusionThe crystal structures ethyl 2-methyl-4-phenyl-5-oxo-5H-indeno [1,2-b] pyridine-3-carboxylate and ethyl 2-methyl-4-(4 chlorophenyl)-5-oxo-5H-indeno [1,2-b] pyridine-3-carboxylate have been investigated in detail. The terminal ethyl group of compound I is disordered. In compound II, the substitution of Cl atom in the phenyl ring alters the configuration of carboxylate group with respect to the pyridine indane ring.

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The crystal structures of 2-methyl-4-phenyl-5-oxo-5H-indeno [1,2-b] pyridine-3-carboxylate (I) and (II) reveal disordered terminal ethyl groups and a substitution of Cl atom in the phenyl

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and crystal structures of 2-methyl-4-aryl-5-oxo-5H-indeno [1,2-b] pyridine carboxylate derivatives

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Citations

One pot synthesis, physicochemical and photophysical investigation of biologically active pyridine-3-carboxylate (ECPC) as probe to determine CMC of surfactants in organized media

ECPC is a biologically active compound that can be used as a probe to determine critical micelle concentrations of anionic and cationic surfactants in organized media, as well as show red shift in absorbance and emission spectrum with increasing solvent polarity.

Optical properties and fluorescence quenching of biologically active ethyl 4-(4-N,N-dimethylamino phenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylate (DDPC) dye as a probe to determine CMC of surfactants

The DDPC dye can be used as a probe to determine the critical micelle concentration of surfactants and its antibacterial activity against various bacteria.

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EIPC dye can be used as a probe to determine the critical micelle concentration of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide in organized media.

Contemporary development in sequential Knoevenagel, Michael addition multicomponent reaction for the synthesis of 4-Aryl-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile

This study demonstrates an efficient, uncatalyzed synthesis of bioactive pyridine derivatives using a three-component sequential multicomponent reaction at ambient temperature without needing ammonium salt.

Direct synthesis of heterocycles via MCRs, using a name reaction

Multicomponent reactions (MCRs) can simplify the synthesis of heterocycles, aiding in rapid identification and optimization of biologically active lead compounds in drug design.