Original scientific paper

https://doi.org/10.5562/cca2339

Synthesis, Crystal and Molecular Structure of Novel Adamantyl Derivatives of N-Aryl Substituted 3-Hydroxy-2-methylpyridine-4-ones

Vesna Petrović Peroković ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Biserka Prugovečki ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Željka Car ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia

Abstract

Two novel potentially bioactive compounds, esters 2-methyl-1-phenylpyridine-4-one-3-yl adamantan-1-ylethanoate (1) and 1-(p-methoxyphenyl)-2-methylpyridine-4-one-3-yl adamantan-1-ylethanoate (2), were synthesized by esterification of adamantan-1-ylacetic acid with appropriate N-aryl substituted 3-hydroxypyridine-4-one derivatives. Both compounds are fully characterized using standard spectroscopic methods. Crystal and molecular structures of 1 and 2 were determined by the single crystal X-ray diffraction method. The crystal packing of both 1 and 2 shows separation of the hydrophobic and hydrophilic regions. The crystal structure of 1 is characterized by the two-dimensional hydrogen bonding layers parallel to (001). The crystal packing of 2 is characterized by hydrogen-bonded chains extended in the direction [010].(doi: 10.5562/cca2339)

Keywords

adamantan-1-ylacetic acid; 3-hydroxypyridine-4-ones; single crystal X-ray diffraction; Steglich esterification

Hrčak ID:

111643

URI

https://hrcak.srce.hr/111643

Publication date:

20.11.2013.

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