Synthesis and Chemical Transformations of 6‐(Morpholine‐4‐sulfonyl)‐quinoline‐2,3,4‐tricarboxylic Acid

Abstract

The article describes an effective synthesis and chemical transformations of 6‐(morpholine‐4‐sulfonyl)‐2,3,4‐quinolinetricarboxylic acid. The key step is the Pfitzinger reaction of 3,3‐dichloro‐2‐oxo‐2,3‐dihydro‐1H‐indole with diethyl 2‐oxosuccinate. Selective 2‐decarboxylation of the tricarboxylic acid followed by reaction of the resulting anhydride with a primary amine led to the formation of the 1,3‐dioxo‐2,3‐dihydro‐1H‐pyrrolo[3,4‐c]quinoline scaffold with interesting pharmacological activity.

Keywords:

• Caspase‐3 inhibitor
• chemical transformation
• Pfitzinger reaction
• pyrrolo[3,4‐c]quinoline

Acknowledgments

The authors thank Caroline T. Williams (Department of Analytical Chemistry, ChemDiv, Inc.) for LCMS and NMR spectral data.