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Paper | Regular issue | Vol 51, No. 12, 1999, pp.2931-2940
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8716
Generality and Scope of the Synthesis of 2-Arylpyrrolo[3,4-b]quinoxaline-1,3-diones from 2,3-Dichloro-N-arylmaleimides. II

Leila Hanaineh-Abdelnour* and Badr A. Salameh

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


Nucleophilic substitution of 2,3-dichloro-N-arylmaleimides (1) and (2) with a series of arylamines gives 2-arylamino-3-chloro-N-arylmaleimides (3) and (4), respectively. When 4 is treated with sodium azide at room temperature, it cyclizes to the 2-(p-methoxyphenyl)pyrrolo[3,4-b]quinoxaline-1,3-diones (5). Under the same conditions, the 2-(p-nitrophenyl) analogue (3) fails to cyclize. Ring closure is also subject to the steric and electronic effects of substituents in the nucleophile.