5-diazo-4-nitroimidazole | 82039-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 5-diazo-4-nitroimidazole
• 英文别名: 4H-Imidazole, 4-diazo-5-nitro-；4-diazo-5-nitroimidazole
• CAS: 82039-91-6
• 化学式: C₃HN₅O₂
• 分子量: 139.073
• InChiKey: ZEPLERLTXFLMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-diazo-4-nitroimidazole 在 盐酸 作用下， 以 水 为溶剂， 反应 730.5h， 以56%的产率得到(9ci)-4-氯-5-硝基-1H-咪唑
  参考文献：
  名称：

  5-重氮-4-硝基咪唑与盐酸的反应

  摘要：

  DOI：

  10.1007/bf02251705
• 作为产物：
  描述：

  5-amino-4-nitroimidazole 在 盐酸 、 sodium nitrite 作用下， 生成 5-diazo-4-nitroimidazole
  参考文献：
  名称：

  摘要：

  Diazotization of 4-R-5-aminoimidazoles (R = CONHAr, CONHAlk, morphohnocarbonyl, or piperidinocarbonyl) with sodium nitrite in aqueous solutions of mineral acids afforded the corresponding 5-diazoimidazoles, whereas the reactions in concentrated tetrafluoroboric acid produced imidazolyl-5-diazonium salts. In the solid phase, diazonium salts are transformed into the corresponding diazo compounds.

  DOI：

  10.1023/a:1025605512301
• 作为试剂：
  描述：

  3-hydrazono-5α-androstan-17β-ol 在 5-diazo-4-nitroimidazole 作用下， 以 乙醇 、 氯仿 为溶剂， 以70%的产率得到3-imino-5α-androstan-17β-ol
  参考文献：
  名称：

  Recyclization of 2-iminocoumarins using nucleophilic reagents. 6. Reaction of 2-iminocoumarin-3-carboxamides with 2-aminobenzophenones

  摘要：

  DOI：

  10.1007/s10593-005-0070-2

文献信息

• Reactions of 6-(Dimethylamino)fulvene with diazoazoles and arene- and azolediazonium salts
  作者：E. V. Sadchikova、D. L. Alekseeva、I. A. Ushakov、V. G. Nenajdenko

  DOI：10.1134/s1070428017100098

  日期：2017.10

  6-(Dimethylamino)fulvene reacted with 3- and 4-substituted 5-diazoazoles, as well as with 4-substituted benzene- and pyrazole-5-diazonium salts, in an aprotic solvent with high regioselectivity at an extremely high rate to give acyclic coupling products at the α-carbon atom of the cyclopenta-1,3-diene fragment. The nature of the diazo component did not affect the reaction direction, rate, or yield

  在非质子传递溶剂中，6-（二甲氨基）富烯烯与3-和4-取代的5-重氮唑盐以及4-取代的苯并吡唑-5-吡唑鎓盐在极高的区域选择性下以极高的速率反应生成无环在环戊-1,3-二烯片段的α-碳原子上的偶合产物。重氮组分的性质不影响反应方向，速率或产率。由are烯二鎓盐得到的偶氮化合物的水解涉及消除二甲基氨基并形成醛，并且它们与吡咯烷的反应导致吡咯烷环取代二甲基氨基。
• Reactivity of diazoazoles and azolediazonium salts in C-azo coupling reactions
  作者：E. V. Sadchikova、V. S. Mokrushin

  DOI：10.1007/s11172-005-0259-7

  日期：2005.2

  The comparative reactivity of heterocyclic diazo compounds and the corresponding diazonium salts in C-azo coupling reactions was studied using imidazole, pyrazole, and triazole derivatives as examples.The reactivities of pyrazole- and imidazole-derived diazonium salts are much lower than those of thiadiazole- and 1,2,4-triazole-derived diazonium salts but higher than those of pyrrole and indole diazo

  以咪唑、吡唑和三唑衍生物为例，研究了杂环重氮化合物和相应的重氮盐在C-偶氮偶联反应中的反应活性。吡唑和咪唑衍生的重氮盐的反应性远低于噻二唑-和 1,2,4-三唑衍生的重氮盐，但高于吡咯和吲哚重氮化合物。
• Synthesis and properties of new nitroimidazoles
  作者：V. S. Mokrushin、I. S. Selezneva、T. A. Pospelova、V. K. Usova、S. M. Malinskaya、G. M. Anoshina、T. É. Zubova、Z. V. Pushkareva

  DOI：10.1007/bf00777271

  日期：1982.3

  5(4)-nitro-4(5)-amino-imidazole (I), we have studied the Schmidt, Hofmann, Lossen, and Curtius rearrangements. The starting m~terials for this purpose were 5(4)-nitroimidazole-4(5)-carboxylic acid (II) If], 5(4)-nitroimidazole-4(5)-carboxamide (IIl)[2], 5(4)-nitroimidazole-4(5)-hydroxamic acid (IV) [3], and 5(4)-nitroimidazole-4(5)-carbonyl azide (V) which we prepared by reaction of 5(4)-nitroimidazo!e-4(5)-carbohydrazide

  在寻找起始材料 5(4)-硝基-4(5)-氨基-咪唑 (I) 的路线时，我们研究了 Schmidt、Hofmann、Lossen 和 Curtius 重排。用于此目的的起始材料是 5(4)-硝基咪唑-4(5)-羧酸 (II)If], 5(4)-硝基咪唑-4(5)-甲酰胺 (IIl)[2], 5 (4)-硝基咪唑-4(5)-异羟肟酸(IV)[3]和我们通过5(4)-硝基咪唑的反应制备的5(4)-硝基咪唑-4(5)-羰基叠氮化物(V) !e-4(5)-碳酰肼 (VI) [4] 与盐酸中的亚硝酸钠。
• Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.
• Synthesis of new heteroaromatic systems: Naphth[2,1-e]imidazo[5,1-c]-1,2,4-triazines and benz[e]imidazo-[5,1-c]-1,2,4-triazines
  作者：M. A. Bezmaternykh、V. S. Mokrushin、E. V. Sadchikova

  DOI：10.1007/bf02269547

  日期：2000.4