130780-12-0Relevant academic research and scientific papers
Synthesis of bis(2,4-diarylimidazol-5-yl) diselenides from N-benzylbenzimidoyl isoselenocyanates
Atanassov, Plamen K.,Zhou, Yuehui,Linden, Anthony,Heimgartner, Heinz
, p. 1102 - 1117 (2007/10/03)
The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isoselenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selenourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.
