113269-12-8Relevant articles and documents
THE FOUR 6-HALO-7-NITROQUINOXALINES
Nasielski-Hinkens, Raymonde,Leveque, Pierre,Castelet, Daniel,Nasielski, Jacques
, p. 2433 - 2442 (2007/10/02)
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 nitro-deiodination.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.