7-氨基-6-硝基苯并二氧化呋咱的合成和表征(英文)  

Synthesis and Characterization of Aminonitrobenzodifuroxan

作　　者：吕连营[1] 欧育湘[1] 王建龙[1] 

机构地区：[1]北京理工大学材料科学与工程学院

出　　处：《合成化学》2004年第2期170-173,共4页Chinese Journal of Synthetic Chemistry

基　　金：NationalDefenseAdvancedResearchFoundation( 1 2 0 60 45 1 867)

摘　　要：以 3 ,5 二硝基苯甲酸 (DNBA)为原料经过 3步反应合成了 7 氨基 6 硝基苯并二氧化呋咱 (ANBDF) :第 1步反应 ,在二氯乙烷惰性溶剂中 ,DNBA与叠氮酸反应并发生Schmidt重排反应生成 3 ,5 二硝基苯胺 ( 1 ) ,产率89.6% ;第 2步反应 ,1在含 1 0 0 %硫酸的硝硫混酸中硝化生成五硝基苯胺 ( 2 ) ,产率 5 1 .1 % ;第 3步反应 ,2与叠氮酸反应 ,不经分离直接进行热解脱氮、Schmidt重排反应 ,得到目标化合物 (ANBDF) ,m .p .2 0 4℃～ 2 0 6℃ ,产率86.8%。用元素分析 ,IR ,1HNMR和MS(FAB)对ANBDF的结构进行了鉴定 ,确证其分子结构中含有氨基、硝基及苯并氧化呋咱环 ,这些基团存在于同一个苯环上 ,且处于同一平面。并对合成反应的机理及反应条件进行了讨论。7-Amino-6-nitrobenzodifuroxan(ANBDF) was prepared through a three-step reaction from starting material 3,5-dinitrobenzoic acid(DNBA): (1)3,5-dinitroaniline(1) was synthesized from the reaction of DNBA and hydrazoic acid in inert solvent 1,2-dichloroethane through Schmidt rearrangement with yield of 89.6%; (2) 1 was subjected to nitration to prepare pentanitroaniline(2) with yield of 51.1%; (3) The title compound was prepared from 2 and sodium azide in acetic acid through denitrogenation and then Schmidt rearrangement with yield of 86.8%, m.p.204℃～206℃. The structure of purified ANBDF was testified by means of elemental analysis, FT-IR, 1H NMR and MS(FAB). ANBDF has amino-group, nitro-group and benzofuroxan ring which are on the benzene ring and on the same plane. The mechanisms of the three mentioned reactions were also discussed.

关 键 词：7-氨基-6-硝基苯并二氧化呋咱 苯并氧化呋咱 合成 表征 反应机理 

分 类 号：O626.2[理学—有机化学]