We prepared a number of di- and trifunctionalized quinolines by selective metalation of chloro-substituted quinolines with metal amides followed by reaction with different electrophiles. Metalation of the C-3 position of the quinolinic ring with lithium diisopropylamide at -70 °C is easy to achieve, whereas reaction with lithium-magnesium and lithium-zinc amides affords C-2 or C-8 functionalized derivatives in a regioselective fashion. These complementary methods could be rationalized by DFT calculations and are convenient strategies toward the synthesis of bioactive quinoline derivatives such as chloroquine analogues.
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Bimetallic Aluminum 5,6-Dihydro-7,7-dimethyl quinolin-8-olates as Pro-Initiators for the ROP of ε-CL; Probing the Nuclearity of the Active Initiator.
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Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Six examples of aluminum 5,6-dihydro-7,7-dimethylquinolin-8-olates, [{2-R¹-7,7-Me₂-8-R²C₉H₆N-8-O}AlR³₂]₂ (R¹ = R² = H, R³ = Me ; R¹ = R² = H, R³ = Et ; R¹ = R² = H, R³ = -Bu ; R¹ = Cl, R² = H, R³ = Me ; R¹ = H, R² = R³ = Me ; R¹ = Cl, R² = R³ = Me ), have been prepared by treating the corresponding pro-ligand (⁻) with either AlMe₃, AlEt₃ or Al(-Bu)₃. All complexes have been characterized by ¹H and C NMR spectroscopy and in the case of and by single crystal X-ray diffraction; dimeric species are a feature of their molecular structures. In the presence of PhCH₂OH (BnOH), ⁻ displayed good control and efficiency for the ROP of ε-CL with almost 100% conversion achievable in 10 min at 90 °C; the chloro-substituted and notably exhibited the lowest activity of the series.
View Article and Find Full Text PDFPhotoisomerization and thermal isomerization of ruthenium aqua complexes with chloro-substituted asymmetric bidentate ligands.
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Department of Applied Chemistry, School of Applied Science, National Defense Academy of Japan Hashirimizu 1-10-20 Yokosuka Kanagawa 239-8686 Japan
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Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo , Av. do Café s/n, Ribeirão Preto, SP 14040-903, Brazil.
We prepared a number of di- and trifunctionalized quinolines by selective metalation of chloro-substituted quinolines with metal amides followed by reaction with different electrophiles. Metalation of the C-3 position of the quinolinic ring with lithium diisopropylamide at -70 °C is easy to achieve, whereas reaction with lithium-magnesium and lithium-zinc amides affords C-2 or C-8 functionalized derivatives in a regioselective fashion. These complementary methods could be rationalized by DFT calculations and are convenient strategies toward the synthesis of bioactive quinoline derivatives such as chloroquine analogues.
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School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
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