CHINESE JOURNAL OF ENERGETIC MATERIALS
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五种呋咱衍生物的新法合成
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(南京理工大学化工学院, 江苏 南京 210094)

作者简介:

高莉(1988-),女,从事含能材料研究。 通迅联系人: 程广斌(1967-),男,从事含能材料及火炸药研究。e-mail: gcheng@mail.njust.edu.cn

通讯作者:

高莉(1988-),女,从事含能材料研究。 通迅联系人: 程广斌(1967-),男,从事含能材料及火炸药研究。e-mail: gcheng@mail.njust.edu.cn

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New Synthetic Route of Five Furazan Derivatives
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(School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094, China) 

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    摘要:

    改进3-(N-2, 4, 6-三硝基苯基)-氨基-4-硝基呋咱、3-氨基-4-(1H-5-四唑基)呋咱、3-硝基-4-(1H-5-四唑基)呋咱、3, 3′-(1H-5-四唑基)-4, 4′-偶氮呋咱及3-氨基-4-(4-氰基-5-氨基-1-1,2,3-三唑基)呋咱的合成方法,反应条件相对温和,产率相应提高:3-氨基-4-硝基呋咱与2, 4, 6-三硝基氯苯(苦基氯)反应以36.1%的收率制得3-(N-2, 4, 6-三硝基苯基)-氨基-4-硝基呋咱;3-氨基-4-氰基呋咱和叠氮基成环得到3-氨基-4-(1H-5-四唑基)呋咱,产率90.9%;以高锰酸钾为氧化剂氧化3-氨基-4-(1H-5-四唑基)呋咱合成出86.8%的3, 3′-(1H-5-四唑基) -4, 4′-偶氮呋咱,以30%的双氧水、钨酸钠及甲磺酸为氧化体系则得到75.6%的3-硝基-4-(1H-5-四唑基)呋咱;3-氨基-4-叠氮基呋咱与丙二腈作用制得3-氨基-4-(4-氰基-5-氨基-1-1,2,3-三唑基)呋咱,产率为91.8%;采用核磁、红外、质谱等分析手段对所合成化合物进行结构表征。

    Abstract:

    The methods of synthesizing 3-(N-2, 4, 6-trinitrophenyl)-amino-4-nitrofurazan, 3-amino-4-(tetrazole-5-yl) furazan, azotetrazolylfurazan, 3-nitro-4-tetrazolylfurazan and 3-amino-4-(4-cyano-5-amino-1, 2, 3-triazol) furazan were improved. The condition of reaction was mild and the yield of target compounds was increased corresponsively. 3-(N-2, 4, 6-trinitrophenyl)-amino-4-nitrofurazan was synthesized by nucleophilic substitution reaction of 3-amino-4-nitrofurazan and 2, 4, 6-trinitro-chlorobenzene(picrylchloride). 3-Amino-4-(tetrazole-5-yl) furazan was obtained from cycloaddition of sodium azide and 3-amino-4-cyanofurazan. 3-Amino-4-(tetrazole-5-yl) furazan was treated with KMnO4 as azo coupling reagent or H2O2, sodium tungstate and methylsulfonic acid as oxidant to afford azotetrazolylfurazan or 3-nitro-4-tetrazolylfurazan, respectively. 3-Amino-4-(4-cyano-5-amino-1, 2, 3-triazol) furazan was prepared by cycloaddition from 3-amino-4-azidofurazan and malononitrile. The yield of these five compounds was 36.1%, 90.9%, 86.8%, 75.6% and 81.8% respectively. These compounds were characterized by 1H NMR, 13C NMR, IR and MS.

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高莉,杨红伟,伍波,等.五种呋咱衍生物的新法合成[J].含能材料, 2013, 21(2):226-229.
GAO Li, YANG Hong-wei, WU Bo, et al. New Synthetic Route of Five Furazan Derivatives[J]. Chinese Journal of Energetic Materials, 2013, 21(2):226-229.

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  • 收稿日期: 2012-07-01
  • 最后修改日期: 2012-09-01
  • 录用日期: 2012-12-03
  • 在线发布日期: 2013-04-26
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