Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles.
An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.
Department of Chemistry, Indian Institute of Science Education and Research Bhopal (IISER), Bhopal, MP 462 023, India.
Shah Jaimin
SJ
Balkrishna
Bhagat Singh
BS
Bhakuni
Deepak
D
Chopra
Sangit
S
Kumar
D001393:Azoles / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D054833:Isoindoles; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D018036:Selenium Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001393:Azoles; D006571:Heterocyclic Compounds; D054833:Isoindoles; D016566:Organoselenium Compounds; D018036:Selenium Compounds; C042986:ebselen; D003300:Copper; D009584:Nitrogen