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Paper | Regular issue | Vol 43, No. 12, 1996, pp.2567-2593
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7516
Synthesis of Dibenzo[d,f]-1,2-selena and -1,2-thiazepin-3-ones Derivatives, Bis-homo-ebselen

Abdelaziz Mohsine* and Léon Christiaens

*Université de Liège, Chimie Organique Hétérocyclique, Institut de chimie, Bat. B6. Sart Tilman 4000 Liège, Belgium

Abstract

Dibenzo[d,f]-1,2-selena and -1,2-thiazepin-3-ones derivatives were prepared from the corresponding 2-alkylselanyl- and 2-alkylsulfanylbiphenyl-2’-carboxamides or their diselenide or disulfide derivatives. These new seven-membered seleno-compounds are homologues of Ebselen (PZ51) (1) which exhibits glutathion peroxidase activity. Bis-homologues of PZ25 (2) were also synthesized. Synthesis of benzo[c]selenocoumarin via a directed ortho metalationbolonic acid cross-coupling reaction and it’s ring-opening reaction are the first step of the synthetic pathway.