par Hinkens, Raymonde ;Levêque, Pierre;Castelet, Daniel;Nasielski, Jacques
Référence Heterocycles, 26, 9, page (2433-2442)
Publication Publié, 1987-09
Article révisé par les pairs
Résumé : 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. © 1987.