1437787-93-3Relevant academic research and scientific papers
Alkyne Versus Ynamide Reactivity: Regioselective Radical Cyclization of Yne-Ynamides
Dutta, Shubham,Mallick, Rajendra K.,Prasad, Rangu,Gandon, Vincent,Sahoo, Akhila K.
, p. 2289 - 2294 (2019)
Ynamides are typically more reactive than simple alkynes and olefins. However, a serendipitous observation revealed a rare case where the reactivity of simple alkynes exceeds that of ynamides. This led to the development of a unique sulfur-radical-triggered cyclization of yne-tethered ynamides, which involves attack of the alkyne by a thiyl radical followed by cyclization with the ynamide. A wide range of novel 4-thioaryl pyrroles that could tolerate common functional moieties and N-protecting groups were expediently constructed by this strategy. The current method contrasts with the typical cyclization of yne-ynamides, which involves the attack of the alkyne moiety by the ynamide core. Control experiments and DFT calculations supported the participation of the sulfur radical in the reaction and the regioselective cyclization. The synthetic potential of the substituted pyrroles is also discussed.
Gold(I)-catalyzed 6-endo-dig hydrative cyclization of an alkyne-tethered ynamide: Access to 1,6-dihydropyridin-2(3H)ones
Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
, p. 9428 - 9433 (2013/07/26)
Hydrate your chemistry! Hydrative cyclization of 5-yne-ynamides in the presence of Echavarren's catalyst and p-toluenesulphonic acid (PTSA)×H2O at room temperature affords an array of 1,6-dihydropyridin-2(3H)one derivatives. Isomerization, epoxidation, and hydrogenation of the double bond and insertion of an extended π-conjugate system into the pyridinone skeleton have been successfully accomplished (see scheme; Ts=tosyl). Copyright
Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes
Liu, Renhe,Winston-Mcpherson, Gabrielle N.,Yang, Zhong-Yue,Zhou, Xin,Song, Wangze,Guzei, Ilia A.,Xu, Xiufang,Tang, Weiping
supporting information, p. 8201 - 8204 (2013/07/04)
Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.
