1296885-53-4Relevant academic research and scientific papers
Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives
Gronnier, Colombe,Boissonnat, Guillaume,Gagosz, Fabien
, p. 4234 - 4237 (2013/09/12)
A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.
2-Substituted-2,3-dihydro-1 H -quinolin-4-ones via acid-catalyzed tandem rupe rearrangement-donnelly-farrell ring closure of 2-(3′-hydroxypropynyl) anilines
Pisaneschi, Federica,Sejberg, Jimmy J. P.,Blain, Cecile,Ng, Wang Hei,Aboagye, Eric O.,Spivey, Alan C.
, p. 241 - 244 (2011/04/16)
A range of 2-substituted 2,3-dihydro-1H-quinolin-4-ones have been synthesized from anilines by a two-step process involving Sonogashira coupling with a propargyl alcohol then acid-catalyzed cyclization of the resulting 2-(3′-hydroxypropynyl)anilines. The cyclization reaction appears to proceed via regioselective rearrangement of the propargyl alcohol to an α,β-unsaturated ketone (Rupe rearrangement) and then 6-endo-trig ring closure (Donnelly-Farrell cyclization). The isolation of the α,β-unsaturated ketone intermediate in one example supports this pathway. Georg Thieme Verlag Stuttgart.
