Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas.
[reaction: see text] Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaquinolines, indoloquinolines, and related ring systems. The intermediacy of an alpha-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked.
Du
Wu
W
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Curran
Dennis P
DP
D003500:Cyclization; D007202:Indicators and Reagents; D011804:Quinolines / Q000138:chemical synthesis*; D013854:Thioamides / Q000737:chemistry*; D013859:Thiocarbamates / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*; D014466:Ultraviolet Rays
D007202:Indicators and Reagents; D011804:Quinolines; D013854:Thioamides; D013859:Thiocarbamates; D013890:Thiourea