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Novel Route to 4-(Adamantan-1-yl)quinoline Derivatives Based on the Friedlander Condensation

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KOZUBKOVA Zuzana ROUCHAL Michal NEČAS Marek VICHA Robert

Rok publikování 2012
Druh Článek v odborném periodiku
Časopis / Zdroj Helvetica Chimica Acta
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
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Doi http://dx.doi.org/10.1002/hlca.201100432
Klíčová slova Friedlander condensation; Quinolines; adamantan-1-yl-; X-Ray crystallography
Popis 2,3,4-Trisubstituted quinolines, substituted with adamantan-1-yl or (adamantan-1-yl)methyl in the 4-position, were prepared from the corresponding admantan-1-yl 2-aminophenyl ketones or admantan-1-ylmethyl 2-aminophenyl ketones and ketones with an a-CH2 group. These reactions were carried out under neat conditions or in toluene, and the products were obtained in moderate-to-excellent yields. The scope and limitations of the examined procedures are discussed. All new compounds are fully characterized by IR and NMR spectroscopy and mass spectrometry. The molecular structures of five new quinolines, obtained via single-crystal X-ray diffraction analyses, are discussed.

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