有机化学 ›› 2010, Vol. 30 ›› Issue (03): 444-448. 上一篇    下一篇

研究简报

3-氨基-4-氧代氰基呋咱捕获与表征

罗义芬*,王伯周,霍欢,刘愆,廉鹏   

  1. (西安近代化学研究所 西安710065)
  • 收稿日期:2008-09-23 修回日期:2009-01-16 发布日期:2010-03-28
  • 通讯作者: 罗义芬 E-mail:luoyiluoyiluoyi204@163.com

Capture and Characterization of 3-Amino-4-oxycyanofurazan

Luo Yifen*,Wang Bozhou,Huo Huan,Liu Qian,Lian Peng   

  1. (Xi'an Modern Chemistry Research Institute, Xi'an 710065)
  • Received:2008-09-23 Revised:2009-01-16 Published:2010-03-28

3,4-双(4-氨基呋咱-3-基)氧化呋咱由活性中间体3-氨基-4-氧代氰基呋咱分子间发生二聚获得, 但3-氨基-4-氧代氰基呋咱不稳定, 无法通过分离、纯化及光谱鉴定证实其存在. 采用4种不同的烯烃与3-氨基-4-氧代氰基呋咱发生1,3-偶极环加成反应得到3-(4-氨基呋咱-3-基)-5-氰基-Δ2-异噁唑啉、3-(4-氨基呋咱-3-基)-5-乙酰氧基-Δ2-异噁唑啉、3-(4-氨基呋咱-3-基)-5-正丁基-Δ2-异噁唑啉及3-(4-氨基呋咱-3-基)-环己烷并-Δ2-异噁唑啉4种Δ2-异噁唑啉衍生物; 采用苯甲酰氯为捕获剂, 与3-氨基-4-氧代氰基呋咱反应获得了3-氨基-4-(N-苯甲酸基氨基羰基)呋咱化合物; 通过红外光谱、核磁共振光谱、质谱、元素分析表征了5种新化合物的结构, 提供了活性中间体3-氨基-4-氧代氰基呋咱存在的间接证据.

关键词: 3-氨基-4-氧代氰基呋咱, 1,3-偶极环加成, 捕获, 表征

3,4-Bis(4-aminofurazan-3-yl)-furoxan was synthesized by the dimerizaion of 3-amino-4-oxy cyano-furazan. However, 3-amino-4-oxycyanofurazan was not steady and could not be separated, purified and confirmed by spectrum. Therefore, 1,3-dipolar cycloaddition reactions of 3-amino-4-oxycyanofurazan were performed with four different olefins, and four novel compounds were synthesized, which were 3-(4-aminofurazan-3-yl)-5-cyano-Δ2-isoxazoline, 3-(4-aminofurazan-3-yl)-5-acetoxy-Δ2-isoxazoline, 3-(4- aminofurazan-3-yl)-5-butyl-Δ2-isoxazoline and 3-(4-aminofurazan-3-yl)-cyclohexyl-Δ2-isoxazoline. At the same time, 3-amino-4-(N-benzoyloxyaminocarbonyl)-furazan was synthesized by the capture of 3-amino- 4-oxycyanofurazan with benzoyl chloride. The structures of the five novel compounds were confirmed by IR, 1H NMR, 13C NMR, MS techniques and elemental analysis. These studies provided indirect evidences for the presence of 3-amino-4-oxycyanofurazan.

Key words: 3-amino-4-oxycyanofurazan, 1,3-dipolar cycloaddition, capture, characterization