Cross-conjugated ω,ω′-bis(dimethylamino) ketones and dinitriles containing a cycloalkane or piperidine fragment: synthesis and study of spectroscopic properties

Autor:	Zh. A. Krasnaya, Vadim V. Kachala, Evgeniya O. Tret’yakova, L. A. Shvedova, S. G. Zlotin, Alexander S. Tatikolov
Rok vydání:	2009
Předmět:	Cycloalkane chemistry.chemical_compound chemistry Absorption spectroscopy Stereochemistry Bathochromic shift Solvatochromism Ionic liquid Hypsochromic shift General Chemistry Piperidine Conjugated system Medicinal chemistry
Zdroj:	Russian Chemical Bulletin. 58:317-321
ISSN:	1573-9171 1066-5285
Popis:	N-Substituted 4-piperidones react with β-dimethylaminoacrolein aminals to give keto-cyanines containing a piperidine ring. A reaction of 3-dimethylamino-1, 1,3-trimethoxypropane with 1-ethoxycarbonylpiperidin-4-ylidenemalononitrile produces a cross-conjugated ω,ω′-bis-(dimethylamino) dinitrile. Its yield is doubled when ionic liquids are used. The spectroscopic properties of the compounds obtained are highly sensitive to the structure: replacement of the C=O group in ketocyanines by the C=C(CN)2 group results in a considerable bathochromic shift of the absorption spectra, while replacement of the central bridging fragment (CH2)3 by (CH2)4 results in a hypsochromic shift. All the compounds obtained exhibit positive solvatochromism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1d4fce6a305e48193df0accb397d6d31 https://doi.org/10.1007/s11172-010-0009-3 Zobrazit plný text záznamu Full text from SpringerLink