Synthesis of 5-azaindoles via a cycloaddition reaction between nitriles and donor-acceptor cyclopropanes.
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.
Moustafa
Mahmoud M Abd Rabo
MM
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7, Canada.
Pagenkopf
Brian L
BL
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
C512290:5-azaindole; D001372:Aza Compounds; D003521:Cyclopropanes; D007211:Indoles; D009570:Nitriles; D010880:Piperidines; D011725:Pyridines; C032727:piperidine; C030797:cyclopropane; C023666:pyridine