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

• Published in: Croatica Chemica Acta 2013-11, Vol.86 (3), p.317-323
• Main Authors: Perokovic, Vesna Petrovic, Prugovecki, Biserka, Car, Zeljka
• Format: Article
• Language: English
• Subjects: 3-hydroxypyridine-4-ones; adamantan-1-ylacetic acid; Chemical compounds; Chemical properties; Chemical synthesis; Crystal structure; Crystals; Cycloalkenes; Diffraction; Methods; Molecular structure; Production processes; single crystal X-ray diffraction; Steglich esterification; Structure
• ISSN: 0011-1643; 1334-417X
• DOI: 10.5562/cca2339

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