3-Allyl-3-hydroxyoxindoles are obtained with high ee in a metal-free catalytic process from isatins. This scaffold has been converted to the natural product chimonamidine.

No abstract

A convenient two step “one‐pot” four‐component synthetic approach was developed for the synthesis of new 6‐arylated 5‐hydroxy‐benzo[a]phenazine derivatives using 2‐hydroxy‐1,4‐naphthoquinone, a variety of aromatic aldehydes, benzene‐1,2‐diamine, and tetronic acid. In all cases, the synthesis proceeded via three key steps including condensation, Michael addition, and tautomerization. The structure of synthesized compounds was elucidated by spectral data. The inhibitory effect of newly synthesized compounds on nitric oxide (NO) production in lipopolysaccharide (LPS)‐ stimulated murine macrophage RAW 264.7 cells was assessed. All products exhibited the highly potential NO production inhibition activity with the IC50 values in the range of 3.68–12.14 μM, indicating the critical role of these compounds in the development of potential anti‐inflammation agents.