Catalysis by triflic acid : synthesis of the indolyquinones as potential antitumor agent

Feyriel Dridi (1, 2) , Didier Villemin (1) , Nathalie Bar (1) , Messaoud Hachemi (2) , Rémi Legay (3, 1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 UMBB - Université M'Hamed Bougara Boumerdes
3 CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie

Trifluoromethanesulfonic acid catalyzes efficiently the conjugate addition of indoles to p-benzoquinones under mild conditions affording the corresponding indolylquinones in high yields with high selectivity. In particular the poorly reactive menadione underwent reaction with indoles under similar conditions to give 3-indolylnaphthoquinones

Mots clés: p-Quinones; indoles; indol-3-ylbenzoquinones; trifluoromethanesulfonic acid

Domaines: Chimie thérapeutique; Chimie organique; Catalyse

Feyriel Dridi, Didier Villemin, Nathalie Bar, Messaoud Hachemi, Rémi Legay. Catalysis by triflic acid : synthesis of the indolyquinones as potential antitumor agent. European Chemical Bulletin, 2015, 4 (10-12), pp.543-590. ⟨10.17628/ecb.2015.4.543-547⟩. ⟨hal-02381054⟩