276884-47-0Relevant academic research and scientific papers
On the validity of au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines
Xia, Yuanzhi,Dudnik, Alexander S.,Li, Yahong,Gevorgyan, Vladimir
, p. 5538 - 5541 (2010)
A mechanism of the Au-catalyzed cycloisomerization of propargylpyridines has been investigated. Both DFT computational and experimental results strongly support generation of a Au-carbene via a cyclization/proton transfer sequence over the previously proposed path involving a Au-vinylidene intermediate. For the β-Si-substituted Au-carbene (G = SiR3), a 1,2-Si migration was shown to be kinetically favored over a 1,2-H shift. This study highlights the importance of alternative pathways that could explain reactivities commonly attributed to an alkyne-vinylidene isomerization in Au catalysis.
Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles
Seregin, Ilya V.,Gevorgyan, Vladimir
, p. 12050 - 12051 (2006)
An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles. Copyright
Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones
Ghazvini, Helya Janatian,Armaghan, Mahsa,Janiak, Christoph,Balalaie, Saeed,Müller, Thomas J. J.
supporting information, p. 7058 - 7062 (2019/11/11)
A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.
Ruthenium-indolizinone complexes as a new class of metalated heterocyclic compounds: Insight into unconventional alkyne activation pathways, revelation of unexpected electronic properties and exploration of medicinal application
Chung, Lai-Hon,Ng, Sze-Wing,Yeung, Chi-Fung,Shek, Hau-Lam,Tse, Sheung-Ying,Lo, Hoi-Shing,Chan, Siu-Chung,Tse, Man-Kit,Yiu, Shek-Man,Wong, Chun-Yuen
, p. 12838 - 12842 (2018/10/02)
The two series of ruthenium-indolizinone complexes prepared by Ru-mediated cyclization of pyridine-tethered alkynes represent the first examples of metalated indolizinone complexes. Joint experimental-theoretical investigation suggests an unconventional 5-endo-dig cyclization pathway as their formation mechanism. They also exhibit moderate cytotoxicity against several human cancer cell lines.
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.
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.
NOVEL OXAZOLIDINONE COMPOUNDS AS ANTIINFECTIVE AGENTS
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Page/Page column 82, (2009/01/20)
The present invention relates to novel oxazolidinone compounds of formula (I) with antibacterial activity, their pharmaceutically acceptable salts, their stereoisomers, their prodrugs, pharmaceutical compositions comprising the same and to their use as therapeutic agents
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.
