609769-60-0Relevant academic research and scientific papers
Copper-Mediated N-Alkynylation of Carbamates, Ureas, and Sulfonamides. A General Method for the Synthesis of Ynamides
Dunetz, Joshua R.,Danheiser, Rick L.
, p. 4011 - 4014 (2003)
(Matrix Presented) A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.
Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and ynamides
Villeneuve, Karine,Riddell, Nicole,Tam, William
, p. 3823 - 3836 (2007/10/03)
Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%). Diastereoselective cycloaddition utilizing chiral cyclic ynamides were also examined and a low to moderate level of asymmetric induction was observed.
Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocydic ynamides
Zhang, Xuejun,Zhang, Yanshi,Huang, Jian,Hsung, Richard P.,Kurtz, Kimberly C. M.,Oppenheimer, Jossian,Petersen, Matthew E.,Sagamanova, Irina K.,Shen, Lichun,Tracey, Michael R.
, p. 4170 - 4177 (2007/10/03)
A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
Ruthenium-catalyzed [2 + 2] cycloadditions of ynamides
Riddell, Nicole,Villeneuve, Karine,Tam, William
, p. 3681 - 3684 (2007/10/03)
(Chemical Equation Presented) Ruthenium-catalyzed [2 + 2] cycloadditions between norbornene and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions, giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%).
