3934-09-6Relevant articles and documents
Oligosubstituted pyrroles directly from substituted methyl isocyanides and acetylenes
Lygin, Alexander V.,Larionov, Oleg V.,Korotkov, Vadim S.,De Meijere, Armin
experimental part, p. 227 - 236 (2009/06/20)
The formal cycloaddition of α-metallated methyl isocyanides 1 onto the triple bond of electron-deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3. The scope and limitations of this reaction (24 examples, 2597 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed CuI-mediated synthesis of 2,3-disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5-88% yield).