A versatile synthesis of diverse 3,4-fused cinnolines via the base-catalysed condensation of 2-amino-2'-nitrobiaryls.
Benzo[c]cinnolines, thieno[3,2-c]cinnolines, pyrido[3,2-c]cinnolines and the previously undescribed quinoxalino[6,7-c]cinnoline ring system are conveniently prepared by a short synthetic route comprised of Suzuki coupling, base-catalysed cyclisation and deoxygenation. The use of tandem borylation-Suzuki coupling further extends the scope of this process to include highly substituted benzo[c]cinnolines.
Slevin
Asa
A
Biovitrum AB, Discovery Research, Retzius Väg 8, SE-112 76, Stockholm, Sweden.
Koolmeister
Tobias
T
Scobie
Martin
M
D001713:Biphenyl Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
D001713:Biphenyl Compounds; D001897:Boronic Acids; D006574:Heterocyclic Compounds, 2-Ring; C476282:cinnoline