Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

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• 作者：Shima Dianat ; Mohammad Mahdavi ; Setareh Moghimi ; Arash Mouradzadegun…
• 关键词：Isocyanide ; based multi ; component reaction (IMCR) ; Ullmann ; type reaction ; Copper ; mediated ; Polycyclic heterocycles ; 2 ; Chloro ; 3 ; formyl ; quinoline
• 刊名：Molecular Diversity
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：19
• 期：4
• 页码：797-805
• 全文大小：750 KB
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• 作者单位：Shima Dianat (1)
  Mohammad Mahdavi (2)
  Setareh Moghimi (2)
  Arash Mouradzadegun (1)
  Abbas Shafiee (2)
  Alireza Foroumadi (2)
  
  1. Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran
  2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Polymer Sciences
  Organic Chemistry
  Pharmacy
  
• 出版者：Springer Netherlands
• ISSN：1573-501X

文摘

2-Chloro-3-formyl quinoline has been applied as an aldehyde moiety in the Groebke–Blackburn–Bienaymé multi-component reaction with isocyanides, 2-aminoazines, and 2-aminoazole to afford the desired adducts which are amenable for further cyclization on the basis of Ullmann-type coupling. The copper iodide-mediated intramolecular C–N bond formation in the second step gave an easy access to a series of imidazo[4\('\),5\('\):4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields. Keywords Isocyanide-based multi-component reaction (IMCR) Ullmann-type reaction Copper-mediated Polycyclic heterocycles 2-Chloro-3-formyl-quinoline