title: Synthesis of 5-azaindoles via a cycloaddition reaction between nitriles and donor-acceptor cyclopropanes.
abstract: A new method for the synthesis of 5-azaindole derivatives is reported. A [3+2] dipolar cycloaddition between nitriles and a 3,4-cyclopropanopiperidine followed by SeO(2) oxidation affords the target compounds in moderate to excellent yields. The divergent nature and cost effectiveness of this method makes it very suitable for combinatorial applications in the pharmaceutical industry.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7, Canada.
authors.forename: Mahmoud M Abd Rabo
authors.initials: MM
authors.lastname: Moustafa
authors.forename: Brian L
authors.initials: BL
authors.lastname: Pagenkopf
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry
chemical_list: C512290:5-azaindole; D001372:Aza Compounds; D003521:Cyclopropanes; D007211:Indoles; D009570:Nitriles; D010880:Piperidines; D011725:Pyridines; C032727:piperidine; C030797:cyclopropane; C023666:pyridine