Synthesis of pyrroles through coupling of enyne-hydrazones with Fischer carbene complexes.
[reaction: see text] The coupling of enyne-imines with Fischer carbene complexes leads to the formation of alkenylpyrrole derivatives. Maximum yields of pyrrole adducts were obtained using N,N-dimethylhydrazones. A mechanism involving alkyne insertion followed by nucleophilic attack of the imine nitrogen at the intermediate alkenylcarbene complex was proposed.
Zhang
Yanshi
Y
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003-8001, USA.
Herndon
James W
JW
D000480:Alkynes / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D006838:Hydrocarbons; D007097:Imines / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D006835:Hydrazones; D006838:Hydrocarbons; D007097:Imines; D011758:Pyrroles; C030011:carbene; D008697:Methane