title: Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds.
abstract: 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[Formula: see text],5[Formula: see text]:4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields.
authors.affiliation: Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran.
authors.forename: Shima
authors.initials: S
authors.lastname: Dianat
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Mahdavi
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Setareh
authors.initials: S
authors.lastname: Moghimi
authors.affiliation: Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran.
authors.forename: Arash
authors.initials: A
authors.lastname: Mouradzadegun
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran. aforoumadi@yahoo.com.
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
mesh_terms: D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003486:Cyanides; D011804:Quinolines; D009584:Nitrogen
keywords: 2-Chloro-3-formyl-quinoline; Copper-mediated; Isocyanide-based multi-component reaction (IMCR); Polycyclic heterocycles; Ullmann-type reaction