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Paper | Regular issue | Vol 26, No. 9, 1987, pp.2433-2442
Published online, 1st January, 1970
DOI: 10.3987/R-1987-09-2433
■ The Four 6-Halo-7-nitroquinoxalines

Raymonde Nasielski-Hinkens, Pierre Levêque, Daniel Castelet, and Jacques Nasielski

*Laboratoire de Chimie Organique CP 160, Université Libre de Bruxelles, Av. F.D. Roosevelt, 50, B-1050 Bruxelles, Belgium

Abstract

The study of relative nucleofugicities of nitro and halogen in quinoxalines required the synthesis of the four 6-halo-7-nitroquinoxalines 2a-d. The fluoro-, chloro- and bromo-derivatives were made from the commercially available or readily accessible 1,2-diamino-4-halobenzenes, using the nitration of the corresponding p-toluenesulfonamides. This scheme failed in the case of the iodo compound because of extensive nitrodeiodination. The synthesis of 6-iodo-7-nitroquinoxaline was finally achieved from m-fluoroiodobenzene by taking advantage of the high reactivity of fluorine, compared to iodine, in 2,4-dinitrohalobenzenes.