Synthesis of 1,4‐Disubstituted and 1‐Substituted β‐Carbolines via 3‐Substituted 2‐Acylindoles

Thees, Katharina; Untergehrer, Martin; Jourjine, Ilya A. P. und Bracher, Franz (2024): Synthesis of 1,4‐Disubstituted and 1‐Substituted β‐Carbolines via 3‐Substituted 2‐Acylindoles. In: European Journal of Organic Chemistry, Bd. 27, Nr. 19

Abstract

β-Carbolines represent a large class of bioactive natural products, whereby most of these alkaloids bear residues at C1, and occasionally at C3, and only limited examples of 1,4-disubstituted β-carbolines are known. In this project we worked out a novel approach to 1,4-disubstituted β-carbolines and performed a comprehensive analysis of the scope and limitations of this methodology. The 1,4-disubstituted β-carbolines were synthesized via 3-substituted 2-acylindoles, for which effective synthesis procedures were developed. Our studies revealed that a broad range of target compounds with electron-withdrawing substituents at C4 are accessible. Limitations of this method arose from competing CH and NH acidities of precursors. Nevertheless, the work described herein provides a unique approach to highly substituted β-carbolines. In addition, intermediates from this route opened a novel approach to 1-substituted β-carbolines utilizing a chemoselective Mo(CO)6-catalyzed amide reduction with tetramethyldisiloxane.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department für Pharmazie - Zentrum für Pharmaforschung
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie ; 600 Technik, Medizin, angewandte Wissenschaften > 610 Medizin und Gesundheit
• ISSN: 1434-193X
• Sprache: Englisch