用核磁共振方法表征6(8)氨基-3H苯[1,2]氧嗪-1,4-二酮  

Nuclear Magnetic Resonacne Characterization of 6(8)-Amino-3H-benzo[d][1,2] oxazine-1,4-dione

作　　者：蒋子江[1] 袁修华[1] 徐经伟[1] 

机构地区：[1]中国科学院长春应用化学研究所国家电化学和光谱研究分析中心,长春130022

出　　处：《分析化学》2006年第4期539-542,共4页Chinese Journal of Analytical Chemistry

摘　　要：用一维1HNMR、13CNMR方法研究了6(8)氨基-3H苯[1,2]氧嗪-1,4二-酮的结构,并通过二维1H-1H同核相关谱(COSY)、13C-1H异核相关谱(HMQC)及13C-1H异核远程相关谱(HMBC)进一步确定了该类化合物的1H谱和13C谱中各谱峰的归属,为研究同类化合物表征提供了依据。As one analogue of thalidomide, N-hydroxy phthalimide has more potent inhibition activity to tumor necrosis factor-α（TNF-α） than thalidomide itself： To get more potent inhibitors to TNF-α, we hope to synthesize amino substituted N-hydroxy phthalimides （3a,3b）. The reported synthesis of 3b needed four steps. We tried heating the mixture of 3-nitro or 4-nitro phthalic anhydrides, hydroxylamine hydrochloride and sodium bicarbonate, the reaction afforded corresponding nitro substituted N-hydrox phthalimides 1 a and 1 b in yield of about 40% indeed, but it afforded other two unreported compounds （2a,2d） and （2b,2c） in yield about 20% at the same time, with each compound having two possible structures 2a, 2d for 4 and 2b, 2c for 5. Catalytic hydrogenation all compounds 1a, lb, 4 and 5 with 10% palladium-carbon afforded corresponding amino substituted compounds 3a,3b, 6 and 7 nearly quantitively. Like compound 4 and 5, both compound 6 and 7 have two possible structures 4a ,4d for 6 and 4b,4c for 7. If the structures of compound 6 and 7 can be determined, the structure of 4 and 5 can also be determined by deducing from 6 and 7. In this study, structures of 6 （ 8 ） -amino-3H-benzo [ d ] [ 1,2 ] oxazine -1,4-dione were studied by nuclear magnetic resonance. Their ^1H and ^13C spectra were assigned completely, which were further confirmed by 2D ^1H-^1H correlation spectrometry （COSY）, ^1H-^13C heteronuclear multiple quantum correlation （HMQC） and ^1H- ^13C long-range heteronuclear multiple bond correlation （HMBC） methods.

关 键 词：核磁共振 6(8)氨基-3H苯[1 2]氧嗪-1 4-二酮 取代基效应 

分 类 号：TQ463.53[化学工程—制药化工]