1258064-80-0Relevant articles and documents
Keteniminium ion-initiated cascade cationic polycyclization
Theunissen, Cdric,Mtayer, Benot,Henry, Nicolas,Compain, Guillaume,Marrot, Jrome,Martin-Mingot, Agns,Thibaudeau, Sbastien,Evano, Gwilherm
, p. 12528 - 12531 (2014)
A novel and efficient keteniminium-initiated cationic polycyclization is reported. This reaction, which only requires triflic acid or bistriflimide as promoters, affords a straightforward entry to polycyclic nitrogen heterocycles possessing up to three co
Cationic polycyclization of ynamides: Building up molecular complexity
Theunissen, Cédric,Métayer, Beno?t,Lecomte, Morgan,Henry, Nicolas,Chan, Hwai-Chien,Compain, Guillaume,Gérard, Phidéline,Bachmann, Christian,Mokhtari, Naima,Marrot, Jérome,Martin-Mingot, Agnès,Thibaudeau, Sébastien,Evano, Gwilherm
, p. 4399 - 4416 (2017/07/10)
Polycyclization reactions are among the most efficient synthetic tools for the synthesis of complex, polycyclic molecules in a single operation from simple starting materials. We report in this manuscript a full account on the discovery and development of a novel cationic polycyclization from readily available ynamides. Simple activation of these building blocks under acidic conditions enables the generation of highly reactive activated keteniminium ions, which triggers an unprecedented cationic polycyclization yielding highly substituted polycyclic nitrogen heterocycles possessing up to seven fused cycles and three contiguous stereocenters.
Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: Second-generation approach to potent ureas bioisosteres
Métayer, Beno?t,Compain, Guillaume,Jouvin, Kévin,Martin-Mingot, Agnès,Bachmann, Christian,Marrot, Jér?me,Evano, Gwilherm,Thibaudeau, Sébastien
, p. 3397 - 3410 (2015/04/22)
(E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
Copper-free sonogashira cross-coupling of ynamides: Easy access to various substituted ynamides from nonsubstituted ynamides
Wakamatsu, Hideaki,Takeshita, Mitsuhiro
experimental part, p. 2322 - 2324 (2010/11/03)
It is demonstrated herein that palladium-catalyzed Sonogashira cross-coupling of ynamides can be accomplished with moderate to good yields of substituted ynamides in the absence of copper salt, and NaOAc plays an important role in this reaction as an addi