934399-73-2Relevant academic research and scientific papers
Palladium-catalyzed carbonylative cyclization/arylation cascade for 2-aroylindolizine synthesis
Li, Zhou,Chernyak, Dmitri,Gevorgyan, Vladimir
supporting information, p. 6056 - 6059 (2013/02/23)
An efficient synthesis of densely substituted 2-aroylindolizines via the palladium-catalyzed carbonylative cyclization/arylation is reported. This transformation proceeds via the 5-endo-dig cyclization of 2-propargylpyridine triggered by an aroyl Pd complex. It produced diversely substituted 2-aroylindolizines in good to excellent yields.
Two-component approach toward a fully substituted N-fused pyrrole ring
Chernyak, Dmitri,Skontos, Cathy,Gevorgyan, Vladimir
supporting information; experimental part, p. 3242 - 3245 (2010/09/30)
(Figure Presented) An efficient two-component palladium-catalyzed arylation/cyclization cascade approach toward a variety of N-fused pyrroloheterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides
Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: Access to polycyclic N-fused heterocycles
Chernyak, Dmitri,Gevorgyan, Vladimir
supporting information; experimental part, p. 5558 - 5560 (2011/02/25)
An efficient palladium-catalyzed intramolecular carbopalladation/ cyclization cascade toward tetra- and pentacyclic N-fused heterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with internal propargylic esters or ethers followed by the 5-endo-dig cyclization leading to polycyclic pyrroloheterocycles in moderate to excellent yields.
Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols
Seregin, Ilya V.,Schammel, Alex W.,Gevorgyan, Vladimir
, p. 6876 - 6883 (2008/09/21)
Two complementary protocols for assembly of multisubstituted N-fused heterocycles have been developed. It was demonstrated that 1,3-disubstituted N-fused heterocycles, including indolizines, pyrroloquinoxalines, and pyrrolothiazoles can easily be synthesized via an exceptionally mild and efficient method involving a novel silver-catalyzed cycloizomerization of propargyl-containing heterocycles. Alternatively, 1,2-disubstituted heterocycles can be accessed through the novel cascade transformation involving an alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, stannyl, or germyl groups. This mild and simple method allows for selective and highly efficient synthesis of indolizines, pyrroloisoquinolines, pyrroloquinoxalines, pyrrolopyrazines, and pyrrolothiazoles.
Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones
Bunnelle, Eric M.,Smith, Cameron R.,Lee, Sharon K.,Singaram, Surendra W.,Rhodes, Allison J.,Sarpong, Richmond
, p. 7008 - 7014 (2008/09/21)
Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles.
Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones
Smith, Cameron R.,Bunnelle, Eric M.,Rhodes, Allison J.,Sarpong, Richmond
, p. 1169 - 1171 (2007/10/03)
(Chemical Equation Presented) Indolizine, pyrrolone, and indolizinone heterocycles are easily accessed via the Pt(II)-catalyzed cycloisomerization or a tandem cyclization/ 1,2-migration of pyridine propargylic alcohols and derivatives. This method provides an efficient synthesis of highly functionalized heterocycles from readily available substrates.
Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol
Seregin, Iiya V.,Schammel, Alex W.,Gevorgyan, Vladimir
, p. 3433 - 3436 (2008/02/12)
A new practical method for the synthesis of N-fused heterocycles via the transition metal-catalyzed cycloisomerization of heterocyles possessing a propagyl group has been developed. This very mild, base- and ligand-free method allows for the synthesis of diverse fused heterocyclic cores in good to excellent yields.
Highly efficient synthesis of functionalized indolizines and indolizinones by copper-catalyzed cycloisomerizations of propargylic pyridines
Yan, Bin,Zhou, Yebing,Zhang, Hao,Chen, Jingjin,Liu, Yuanhong
, p. 7783 - 7786 (2008/03/12)
(Chemical Equation Presented) The copper-catalyzed cycloisomerizations of 2-pyridyl-substituted propargylic acetates and its derivatives are described, which offer an efficient route to C-1 oxygenated indolizines with a wide range of substituents under mild reaction conditions. The presented method could be readily applied to the synthesis of indolizinones through a cyclization/1,2- migration of tertiary propargylic alcohols.
