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Novel one-pot synthesis of functionalized quinolines from isocyanides, aniline, and acetylene dicarboxylate via cu-catalyzed intramolecular C─H activation reactions

Nematpour, M ; Sharif University of Technology | 2019

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  1. Type of Document: Article
  2. DOI: 10.1002/jhet.3477
  3. Publisher: HeteroCorporation , 2019
  4. Abstract:
  5. The one-pot synthesis of a novel class of substituted quinoline derivatives with good yields is achieved via the Cu-catalyzed intramolecular C─H activation reaction between isocyanides, aniline, and acetylene dicarboxylate in MeCN at room temperature. The existence of one-pot conditions, availability of a starting material-catalyst, the absence of column chromatography, and a high yield of products are among the advantages of this method. The structures are confirmed spectroscopically (1H NMR and 13C NMR, IR, and EI-MS) and through elemental analyses
  6. Keywords:
  7. Acetylene dicarboxylate ; Aniline ; Carbon ; Copper ; Cyanide ; Di tert butyl 6 chloro 4 [(4 chlorophenyl)amino]quinoline 2,3 dicarboxylate ; Di tert butyl 6 methyl 4 (phenylamino)quinoline 2,3 dicarboxylate ; Dicarboxylic acid derivative ; Diethyl 4 (tert butylamino)quinoline 2,3 dicarboxylate ; Diethyl 4 [(4 bromophenyl)amino] 6 methylquinoline 2,3 dicarboxylate ; Diethyl 6 bromo 4 (phenylamino)quinoline 2,3 dicarboxylate ; Dimethyl 4 (cyclohexylamino) 6 methylquinoline 2,3 dicarboxylate ; Dimethyl 4 (cyclohexylamino) 6 nitroquinoline 2,3 dicarboxylate ; Dimethyl 4 (phenylamino)quinoline 2,3 dicarboxylate ; Dimethyl 4 (tert butylamino)quinoline 2,3 dicarboxylate ; Dimethyl 4 [(4 bromophenyl)amino]quinoline 2,3 dicarboxylate ; Dimethyl 4 [(4 nitrophenyl)amino]quinoline 2,3 dicarboxylate ; Hydrogen ; Isocyanide ; Quinoline derivative ; Unclassified drug ; Carbon nuclear magnetic resonance ; Catalysis ; Chemical modification ; Chemical reaction ; Column chromatography ; Drug structure ; Drug synthesis ; Dlectron impact mass spectrometry ; Dlemental analysis ; Infrared spectroscopy ; Intramolecular activation reaction ; One pot synthesis ; Physical chemistry ; Proton nuclear magnetic resonance ; Rreaction analysis ; Room temperature
  8. Source: Journal of Heterocyclic Chemistry ; Volume 56, Issue 4 , 2019 , Pages 1254-1259 ; 0022152X (ISSN)
  9. URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/jhet.3477