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Communication | Regular issue | Vol 14, No. 8, 1980, pp.1107-1110
Published online, 1st January, 1970
DOI: 10.3987/R-1980-08-1107
Synthesis of a New Azacyclazine, Indolizino[3,4,5,6-cde]quinoxaline

Shuji Kanemasa,* Seigo Kobira, and Shoji Kajigaeshi

*Department of Industrial Chemsitry, Faculty of Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan


A new peripheral azomethine ylid 1,3-dipole, anhydro 3H-pyrido[1,2,3-de]quinoxalin-4-ium hydroxide, was generated from the pyridoquinoxalinium bromide and reacted with dimethyl acetylenedicarboxylate giving the indolizino[3,4,5,6-cde]quinoxaline in quantitative yield. With electron-deficient olefins such as diethyl fumarate and N-benzylmaleimide, the corresponding [4+2] cycloadducts were formed, which were then dehydrogenated with p-chloranil into the similar heterocycles in fair yields.