Microwave‐Assisted Synthesis of Heterocycles from Aryldiazoacetates. Issue 45 (17th November 2020)

• Record Type: Journal Article
• Authors: Kristoffersen, Tone; Elumalai, Vijayaragavan; Starck, Eliot; Cousin, Étienne; Wagner, Lucille J.; Hansen, Stephanie R.; Hansen, Jørn H.
• Is Part Of: European journal of organic chemistry. Issue 45(2020)
• Page Start: 7069
• Page End: 7078
• Publication Date: 2020-11-17
• Subjects: Microwave -- Diazoacetates -- N–H insertion -- Dihydroquinoxalinones -- Quinoxalines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202001155
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Herein, we describe a rapid microwave‐assisted, metal‐free synthesis of substituted quinoxalinones and quinoxalines using the carbene‐mediated reaction between aryldiazo esters and 1, 2‐diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin‐2‐ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2, 3‐diarylquinoxalines, bis‐quinoxalines as well as novel quinoxaline‐substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox. Abstract : Microwave‐superheated solutions of aryldiazoacetates and 1, 2‐diamines mixed in toluene yield rapid access to quinoxalinones and quinoxalines without the use of catalysts, additives or otherwise complicated reaction conditions.