title: Sc(OTf)3-catalyzed bicyclization of o-alkynylanilines with aldehydes: ring-fused 1,2-dihydroquinolines.
abstract: A Sc(OTf)3 -catalyzed cascade Prins-type cyclization reaction of o-alkynylanilines, bearing a hydroxy or amine functionality, with aldehydes affords 1,2-dihydroquinoline derivatives having an extra fused ring efficiently under mild reaction conditions. It is interesting to observe the reversed reactivity in the highly selective formation of 1,2-dihydroquinoline derivatives instead of the formation of the usually favored indole derivatives.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China).
authors.forename: Can
authors.initials: C
authors.lastname: Zhu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C544515:1,4-dihydroquinoline; D000447:Aldehydes; D000814:Aniline Compounds; D008698:Mesylates; D011804:Quinolines; C436603:scandium triflate; D012538:Scandium
keywords: aldehydes; amine; cyclization; heterocycles; scandium