A variety of diversely substituted aryl triflate esters were efficiently deprotected to the parent phenols by exposure to cesium carbonate in toluene. This procedure proved highly compatible with existing functional groups.
Green, Alice E.,Agouridas, Vangelis,Deniau, Eric
supporting information
p. 7078 - 7079
(2013/12/04)
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
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.
Pisaneschi, Federica,Sejberg, Jimmy J. P.,Blain, Cecile,Ng, Wang Hei,Aboagye, Eric O.,Spivey, Alan C.
supporting information; experimental part
p. 241 - 244
(2011/04/16)
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