338465-82-0Relevant academic research and scientific papers
3H-pyrroles, alkylidene-pyrrolines and functionalized pyrrolidines by radical cyclization of β-allenyliminyl radicals
Depature, Michael,Grimaldi, Jacques,Hatem, Jacques
, p. 941 - 946 (2001)
In this work, we show that the tin hydride-mediated reaction of allene-tethered dithiosemicarbazides 4 is a convenient method for the preparation of five-membered unsaturated nitrogen heterocycles. The sulfur-directed intermolecular attack of the tin radical at the semicarbazide moiety leads to an allene-tethered iminyl radical, which then undergoes a 5-exo-dig cyclization leading to both the 3H-pyrroles 5 and the alkylidene pyrrolines 6; thermal isomerization of 5 to 6 occurs in some cases.
