Synthesis of quinoxalines by cyclization of α-arylimino oximes of α-dicarbonyl compounds

✍ Scribed by N.P Xekoukoulotakis; C.P Hadjiantoniou-Maroulis; A.J Maroulis

• Book ID: 104211392
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 57 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01847-5

✦ Synopsis

Heating the title compounds 1 at reflux in acetic anhydride yields quinoxalines 3 and 4 via a presumed aryliminoiminyl radical 5, resulting from homolytic cleavage of the N O bond in the intermediate ester 2. The observed regioselectivity of the reaction is also rationalized by implicating such a radical.