Arylation of quinoxalinones at room temperature under metal and base free-conditions

• Published in: Monatshefte für Chemie Vol. 155; no. 6; pp. 613 - 619
• Main Authors: Badhani, Gaurav, Adimurthy, Subbarayappa
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.06.2024; Springer Nature; Springer Nature B.V
• Subjects: Analytical Chemistry; Base metal; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Functional groups; Inorganic Chemistry; Organic Chemistry; Original Paper; Physical Chemistry; Physical Sciences; Room temperature; Science & Technology; Theoretical and Computational Chemistry; Arylation; Regioselective; Quinoxalinone; Aryldiazonium salt; Catalyst-free reaction; DESIGN; POTENT; C-H ARYLATION; SULFENYLATION; QUINOXALIN-2(1H)-ONES; INHIBITORS
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-024-03188-2

A mild and efficient method for the arylation of quinoxalinones are described using aryldiazonium tetrafluoroborates as aryl source. Reactions proceeds at room temperature in a short reaction time of 1 h without metal catalysts and bases. Broad functional group tolerance was observed with good yields of products even at gram scale reaction. Control experiments suggest that the reactions proceed through a radical pathway. Furthermore, the present protocol applied for the successive synthesis of three biologically active molecules. Overall, the method offers a convenient and versatile approach for the synthesis of arylated quinoxalinones. Graphical abstract