486999-98-8Relevant academic research and scientific papers
Intra- and intermolecular trapping of cyclopentapyrazine carbenes derived from 1,2-dialkynylimidazoles
Nadipuram, Asha K.,Kerwin, Sean M.
, p. 353 - 356 (2007/10/03)
The thermolysis of 1,2-dialkynylimidazoles in benzene solution affords high yields of 7-phenyl-5H-cyclopentapyrazines, which presumably form by solvent trapping of cyclopentapyrazine carbene intermediates. In cases where dialkynylimidazole contains side chains that can participate in intramolecular carbene C-H insertion or olefin addition, these processes compete with solvent addition to afford novel tri- and tetracyclic pyrazines, which can be obtained in good yield when the thermolysis is carried out in hexafluorobenzene.
Synthesis and thermolysis of heterocyclic 3-aza-3-ene-1,5-diynes(1).
Nadipuram, Asha K,David, Wendi M,Kumar, Dalip,Kerwin, Sean M
, p. 4543 - 4546 (2007/10/03)
[reaction: see text] Simple, acyclic 3-aza-3-ene-1,5-diynes undergo an aza-Bergman rearrangement to a fleeting 2,5-didehydropyridine (2,5-ddp) intermediate that rapidly ring-opens to beta-alkynylacrylonitrile products. In an effort to access longer-lived 2,5-ddp intermediates, we have prepared heterocyclic 3-aza-3-ene-1,5-diynes. The thermolysis of one such heterocyclic aza-enediyne does not afford products derived from trapping a 2,5-ddp intermediate but rather cyclopropanes that appear to arise from a carbene intermediate and a product that appears to be a trapping product from a 2,3-ddp intermediate.
