CAJ | 학술논문

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100%硫酸的硝硫混酸中硝化生成五硝基苯胺(2),产率51.1%;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.204℃～206℃,产率86.8%.用元素分析,IR,1H NMR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.
이3,5-이초기분갑산(DNBA)위원료경과3보반응합성료7-안기-6-초기분병이양화부찰(ANBDF):제1보반응,재이록을완타성용제중,DNBA여첩담산반응병발생Schmidt중배반응생성3,5-이초기분알(1),산솔89.6%;제2보반응,1재함100%류산적초류혼산중초화생성오초기분알(2),산솔51.1%;제3보반응,2여첩담산반응,불경분리직접진행열해탈담、Schmidt중배반응,득도목표화합물(ANBDF),m.p.204℃～206℃,산솔86.8%.용원소분석,IR,1H NMR화MS(FAB)대ANBDF적결구진행료감정,학증기분자결구중함유안기、초기급분병양화부찰배,저사기단존재우동일개분배상,차처우동일평면.병대합성반응적궤리급반응조건진행료토론.
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.