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

Vinodh Kumar, Ramesh Pandian, Edayadukka Naushad , Günther H.J. Peters, P. M. Nanjappagounder

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Background: Hantzsch 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.Results: The 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 R2 2 (16) dimer running along 011 direction.Conclusion: The 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
    Original languageEnglish
    Article number34
    JournalChemistry Central Journal
    Volume8
    Issue number1
    ISSN1752-153X
    DOIs
    Publication statusPublished - 2014

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