Figure 3

Preparation of ebselen, its derivatives and their ‘dimeric’ form analogues 1–33. Reagents and conditions: (a) (i) aq. HCl, (ii) NaNO2, − 7 to + 7 °C, (b) (i) NaSeSeNa, MeOH, NaOH or LiSeSeLi, THF, HMPTA, − 7 to + 5 °C, (ii) aq. HCl, (c) 7 equiv SOCl2, cat. (DMF), benzene, reflux, (d) RNH2, Et3N, MeCN or DCM, (e) 3.5 equiv SOCl2, cat. (DMF), benzene, reflux, (f) RNH2, Na2CO3, DCM, (g) H2N-NH2∙H2O, MeOH, reflux. (Carried out in accordance with Refs.60,62,63,64.