一锅法合成含氨基葡萄糖分子片段的1,4-二取代氨基脲衍生物  

One-Pot Synthesis of 1,4-Disubstituted Semicarbazide Derivatives Containing Glucosamine Molecular Fragments

作　　者：刘玮炜[1,2,3] 张强[2,4] 程峰昌 李曲祥 霍云峰[1] 

机构地区：[1]淮海工学院化学工程学院,江苏连云港222005 [2]中国矿业大学化工学院,江苏徐州221116 [3]江苏省海洋资源开发研究院,江苏连云港222005 [4]浙江新和成股份有限公司,浙江新昌312500

出　　处：《精细化工》2014年第10期1245-1249,1283,共6页Fine Chemicals

基　　金：江苏省高校自然科学研究重大项目(10KJA170003);江苏省高校科研成果产业化推进项目(JHB2012-60);连云港市科技攻关项目(CG1105);江苏高校优势学科建设工程资助项目~~

摘　　要：为了需求新的含有氨基葡萄糖分子片段的氨基脲类化合物,以1,3,4,6-四-O-苄基-β-D-氨基葡萄糖盐酸盐,固体光气和酰肼为原料,一锅法合成了11种1,4-二取代氨基脲衍生物。对于选用脂肪酰肼、芳香酰肼、杂环酰肼以及苯磺酰肼等代表性反应物来合成目标产物,该方法有较强的适应性,并且以乙酰肼为模型反应物,对实验条件进行优化,得到最优合成条件为:在固体光气过量条件下,反应溶剂为1,2-二氯乙烷,反应摩尔配比为n[反应物(Ⅰ)]∶n(乙酰肼)=1∶1.2,反应温度为常温(20℃),反应时间为2.5 h。目标化合物结构经IR,1HNMR,HRMS(ESI)进行了表征。In response to the demand for new compounds containing semicarbazide glucosamine molecule fragments, eleven kinds of 1,4-disubstituted semicarbazide derivatives were synthesized from 1,3,4,6-tetra-O-benzyl-β-D-glucosamine hydroehloride, solid phosgene and hydrazine. This method had high adaptability for synthesis with such representative reactants as fatty hydrazide, aromatic hydrazide,heterocyelic hydrazide, and sulfonyl hydrazide. Aeetyl hydrazide was used as the model to sort out the experimental conditions. The optimum reaction conditions were ： under the condition of two- phase of 1,2-diehloroethane and saturated sodium bicarbonate solution,in the presence of excess solid phosgene,the reaction molar ratio of （ I ） and acetohydrazide was 1：1.2,the reaction temperature was 20 ℃, and the reaction time was 2. 5 hours. The structures of the target products were confirmed by IR spectroscopy, 1^HNMR and ESI-MS spectra.

关 键 词：1 3 4 6-四-O-苄基-β-D-氨基葡萄糖盐酸盐 固体光气 脲类衍生物 一锅法 医药与日化原料 

分 类 号：R914.4[医药卫生—药物化学]