Synthesis of new fluorine-containing derivatives of quinoxaline 1,4-dioxides and condensed systems derived from them

The Beirut reaction of 5,6-difluorobenzofuroxan with 1,3-diketones, β-ketoesters, and amides produces 6,7-difluoroquinoxaline 1,4-dioxides. The condensation of 2-ethoxycarbonyl-6,7-difluoro-3-methylquinoxaline 1,4-dioxide is studied. Fluorinated furo[3,4-b]- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides are synthesized and further functionalized by nucleophilic substitution of fluorine and reduction of the N-O bond. Dedicated to Professor Henk van der Plas on his 70th birthday. Ural's State Technical University, Ekaterinburg 62002, Russia; e-mail: azine@htf.rcupi.e-burg.su. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 520–531, April, 1999.