Synthesis and antidepressant-like activity of selenophenes obtained via iron(iii)PhSeSePh-mediated cyclization of Z-selenoenynesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1ob06548c

We present here the synthesis and antidepressant-like action of a series of 2,5-disubstituted-3-(organoseleno)-selenophenes prepared by a novel synthetic route, the FeCl 3 diorganyl dichalcogenide-mediated intramolecular cyclization of ( Z )-chalcogenoenynes. The cyclized products were obtained in good yields. The results showed that 2c , 2d , 2e and 2o , evaluated in the mouse forced-swimming test, elicited an antidepressant-like activity. The studies clearly show that the phenyl group at the 2-position and an organoselenium group at the 3-position of the selenophene ring are essential for the antidepressant-like activity of selenophenes. A close inspection of the results also revealed that the fluorophenyl portion in the organoselenium group is fundamental for the antidepressant-like action of this class of organochalcogens. We present the antidepressant-like action of 2,5-disubstituted-3-(organoseleno)selenophenes prepared by a novel synthetic route, the intramolecular cyclization of ( Z )-chalcogenoenynes.