含有α-氨基醇片段的2H-1,4-苯并噁嗪类化合物的合成研究

Synthesis of 2H-1,4-benzoxazines with the α-amino alcohol segment

目的合成含有α-氨基醇片段的2H-1,4-苯并噁嗪类化合物。方法以邻硝基苯酚类化合物为原料,经与2-溴代羧酸酯的Williamson醚合成、还原硝基成氨基、分子内酯胺解关环酰基化、LiBEt3H还原得到目标化合物。结果与结论合成了9个α-氨基醇型2H-1,4-苯并噁嗪类化合物,其结构经1H-NMR和MS谱表征。该合成方法适合2位无取代或小结构取代的该类型化合物的合成。

The 2H-1,4-benzoxazine compound is present in many natural products which not only has antineoplastic,antibiotic,anti-inflammatory,regulating central nervous system,treating cardiovascular diseases and other good pharmaceutical activities,but also can be used as a herbicide in agriculture.As a new kind of heterocyclic compounds,2H-1,4-benzoxazines have attracted considerable attention in drug research fields.There are few reports about the chemical synthesis of this kind of compounds with alpha-amino alcohol segment.We design a synthetic method for this kind of compounds,which prepared from o-nitrophenol compounds,reaction with 2-bromocarboxylic ester,followed by the reduction of the nitro group,after the aminolysis of lactone and are duction step through LiBEt3H.Finally we obtained nine derivatives ofα-amino alcohol-2H-1,4-benzoxazine(7 a-7 e,8 a-8 d),whose structures were characterized by 1H-NMR and MS spectra.This method is suitable for the synthesis of this kind of compounds which are unsubstituted or small group substituted at the 2-position.