1298088-57-9Relevant academic research and scientific papers
An unconventional sulfur-to-selenium-to-carbon radical transfer: Chemo-and regioselective cyclization of yne-ynamides
Dutta, Shubham,Prabagar,Vanjari, Rajeshwer,Gandon, Vincent,Sahoo, Akhila K.
supporting information, p. 1113 - 1118 (2020/03/11)
An uncommon sulfur → selenium → carbon radical transfer process is employed to develop an unprecedented selenyl radical-mediated regioselective cyclization of yne-tethered-ynamides. Density functional theory studies and HRMS experiments are used to establish a reactivity scale between thiyl and selenyl radicals. The unique features of this transformation include, (1) the chemoselective reactivity of RSe over RS, (2) regioselective RSe attack on alkyne over ynamide, (3) 5-exo-dig cyclization of yne-ynamide to unusual 4-selenyl-pyrroles, and (4) the green synthetic method. The reaction of methyldiselenide with yne-ynamides to methylselenopyrroles is also described.
Cu(I)-catalyzed oxidative cyclization of enynamides: Regioselective access to cyclopentadiene frameworks and 2-aminofurans
Shen, Wen-Bo,Tang, Xiang-Ting,Zhang, Ting-Ting,Liu, Si-Yu,He, Jiang-Man,Su, Tong-Fu
supporting information, p. 6799 - 6804 (2020/09/15)
An efficient Cu(I)-catalyzed oxidative cyclization of alkynyl-tethered enynamides for the construction of fused bicyclic cyclopentadiene derivatives is disclosed. The cascade proceeds through alkyne oxidation, carbene/alkyne metathesis, and formal (3 + 2)
Gold-Catalyzed Annulations of N-Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities
Hsu, Yu-Chen,Hsieh, Shu-An,Liu, Rai-Shung
supporting information, p. 5288 - 5297 (2019/03/26)
Gold-catalyzed annulation of N-propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N-propargyl ynamide, its resulting α-imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3-b]quinoline derivative after treatment with p-toluenesulfonic acid. For an internal alkyne, its α-imino gold carbene reacts with a tethered alkyne via either a vinyl cation or an alkenylgold carbene; both paths ultimately lead to a 4-ketone-2-aminopyrrole derivative. Our mechanistic analysis indicates that water is a better nucleophile than anthranil for terminal ynamides, whereas water and anthranils are equally reactive for internal ynamides.
Dimethyl Sulfoxide and N-Iodosuccinimide Promoted 5-exo-dig Oxidative Cyclization of Yne-Tethered Ynamide: Access to Pyrrolidones and Spiro-pyrrolidones
Prabagar,Nayak, Sanatan,Prasad, Rangu,Sahoo, Akhila K.
, p. 3066 - 3069 (2016/07/13)
An unprecedented metal-free dimethyl sulfoxide (DMSO) and N-iodosuccinimide mediated regioselective 5-exo-dig oxidative cyclization of an in situ generated enol equivalent of amides from ynamides bearing internal alkynes is demonstrated. The reaction allows easy access to functionalized pyrrolidone skeletons. Pyrrolidones having 3-o-biaryl motifs successfully undergo intramolecular electrophilic cyclization with the α,β-unsaturated olefin, furnishing spiro-pyrrolidone motifs. A one-pot sequential 5-exo-dig cyclization of the yne-tethered ynamides, followed by electrophilic cyclization of the pyrrolidone, is presented. The role of DMSO in the transformation is clarified, and a tentative reaction pathway is proposed.
