Ruthenium(II)‐Catalyzed C–H Alkenylation of Quinones: Diversity‐Oriented Strategy for Trypanocidal Compounds

Abstract

Ruthenium(II)‐catalysis enabled C–H alkenylations of unactivated naphthoquinones for the preparation of A‐ring‐modified naphthoquinoidal compounds with activity against Trypanosoma cruzi, the parasite causing Chagas disease. The present study encompasses C–H alkenylation by weak O‐coordination by means of ruthenium(II) carboxylates. This method provided an efficient and versatile tool towards a diversity‐oriented strategy for the preparation of compounds with a relevant biological profile.

Ruthenium(II)‐Catalyzed Double Annulation of Quinones: Step‐Economical Access to Valuable Bioactive Compounds

“…However,f urther experimentation revealed DCE as the optimal solvent for this transformation, and, consequently, we decided to probe the presence of additives to generate a cationic ruthenium(II) catalyst. Here, KPF 6 ,K OAc, NaOAc, and NaOPivw eree valuated as additives (entries [11][12][13][14]. Further refinementl ed to the reaction conditions outlined in entries 15 and 18, delivering product 3a in 80 %y ield (see Supporting Information for experimental details).…”

The Different Facets of Metal‐Catalyzed C−H Functionalization Involving Quinone Compounds

“…Our group has also reported a cationic Ru(II)‐catalysed method for the benzenoid C−H alkenylation of naphthoquinones (Scheme 58). [94] Whereas a RuH 2 (CO)(PPh 3 ) 3 catalyst previously afforded alkylated quinones from olefins in a redox‐neutral process, the electron deficient alkenes employed here provided olefinated products in an oxidative process. The proposed mechanism entails activation of the ruthenium precatalyst by silver and copper salts, followed by C−H metalation of the naphthoquinone substrate to afford a ruthenacycle.…”

Structure-based identification of naphthoquinones and derivatives as novel inhibitors of main protease Mpro and papain-like protease PLpro of SARS-CoV-2

“…Compounds containing sulfur, as sulfoxides and sulfones [98,99], selenium [100], iodine [47], amines, bromine, hydroxyls, alkenes, among other substituent groups [46,[101][102][103][104][105][106][107] were studied and evaluated according to their potential to act as anti-SARS-CoV-2. Imine derivatives were also targeted in our studies and were placed in group 6 [67].…”