Synthesis and structural characterization by NMR and X-ray of new Morita-Baylis-Hillman adducts derived from 7-chloroquinoline
| Autor: | Rhuan Karlos Santos Mendes, Claudio G. Lima-Junior, João Paulo Gomes de Oliveira, Felipe T. Martins, Mário L. A. A. Vasconcellos, Everton da Paz Silva, Fábio P.L. Silva, Guilherme S. Caleffi, Tayná Rodrigues Olegário |
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| Rok vydání: | 2017 |
| Předmět: |
Acrylate
010405 organic chemistry Organic Chemistry DABCO 010402 general chemistry Acryloyl chloride 01 natural sciences Medicinal chemistry 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Nucleophilic aromatic substitution Yield (chemistry) Moiety Ethyl acrylate Organic chemistry Ethylene glycol Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1133:358-368 |
| ISSN: | 0022-2860 |
| Popis: | Herein we describe the design, synthesis and structural characterization by NMR and X-ray of new molecular hybrids 4a - 4c containing the nitroaromatic MBHA moiety and the 7-chloroquinoline pharmacophores, linked by an aliphatic spacer as a model for antiprotozoal drugs. Firstly, the 4,7-dichloroquinoline ( 7 ) reacted with excess of ethylene glycol, through a SNAr promoted by t -BuOK, to prepare the 2-(7-chloroquinolin-4-yloxy)ethanol ( 6 ) in 98% isolated yield. Then, the novel 2-(7-chloroquinolin-4-yloxy) ethyl acrylate ( 5 ) was synthesized in 78% isolated yield by reacting the alcohol ( 6 ) with acryloyl chloride and TEA in CH 2 Cl 2 . Finally, this acrylate ( 5 ) reacted with o -nitrobenzaldehyde, m -nitrobenzaldehyde and p -nitrobenzaldehyde through Morita-Baylis-Hillman reactions promoted by DABCO at room temperature, using t -BuOH:Water (9:1) as solvent, to afford the new hybrids 4a-4c in 73–76% isolated yields. Three-dimensional structures were characterized in both monomeric and intermolecular packing by X-Ray experiments. |
| Databáze: | OpenAIRE |
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