CAS: 4531-54-8; 1-Methyl-4-Nitro-1H-Imidazol-5-Amine

该化合物是其imidazole环结构,即五人组成的含有两个氮原子的热循环化合物,该物质在Iidazole环的4个位置上有一个甲基组和一个硝化物组,在5位置上有一个氨基质组.这些功能组有助于其化学反应和在各个领域的潜在应用,包括药物和农用化学.该化学组的存在通常具有电子哲学特性,因此是进一步化学修改的候选体.此外,该化合物可能展示生物活动,可以在药化学领域加以探索.其溶性,稳定性和再活性可能因溶剂和环境条件而不同.应当查阅处理和储存的安全数据,因为与硝基组的化合物有时对热和冲击十分敏感.

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CAS号3034-41-1 1-甲基-4-硝基咪唑 | CAS号4897-25-0 1-甲基-5-氯-4-硝基咪唑

合成工艺路线路线简述

  • 合成目标产物 1H-Imidazol-5-Amine,1-Methyl-4-Nitro-(9CI) 主要起始原料 5-Chloro-1-Methyl-4-Nitroimidazole
  • (文献来源)合成步骤主要原料 5-Chloro-1-Methyl-4-Nitroimidazole
📜1-甲基-4-硝基咪唑置于ammonium Pyrrolidinedithiocarbamate体系中,用36%的收率获得产物(9CI)-1-甲基-4-硝基-1H-咪唑-5-胺
参考文献:Nitroarylamines Via The Vicarious Nucleophilic Substitution Of Hydrogen: Amination,Alkylamination,And Arylamination Of Nitroarenes With Sulfenamides
标题:Nitroarylamines Via The Vicarious Nucleophilic Substitution Of Hydrogen: Amination,Alkylamination,And Arylamination Of Nitroarenes With Sulfenamides
摘要:A New Reaction Of Sulfenamides With Electrophilic Arenes Under Basic Conditions Is Described. The Sigma Adducts Formed From Nitroarenes And The Anions Of Sulfenamides Undergo Elimination Of Thiol To Produce The Corresponding O-And/or P-Nitroanilines. This Reaction Is Analogous To The Known Alkylation And Hydroxylation Of Nitroarenes Via The Vicarious Nucleophilic Substitution Of Hydrogen (Vns). The Reaction Gives Access To A Wide Range Of Substituted Nitroanilines,Nitronaphthylamines,And Aminoheterocycles. By Means Of The Reaction With N-Alkryl-And N-Arylsulfenamides,It Is Possible To Obtain N-Alkylnitroanilines And Nitrodiarylamines. By Varying The Structure Of Sulfenamide And The Reaction Conditions,Particularly The Nature And Concentration Of The Base,It Is Possible To Control The Orientation Of Amination.
DOI:10.1021/jo970582B

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主要参考文献

参考标题:A Catalyst And Additive-Free Three-Component Reaction Of Highly Electrophilic Azides With Cyclic Ketones And Cycloaliphatic Amines. Synthesis Of Novel N-Heteroaryl Amidines
作者:Ilya Efimov,Nikolai Beliaev,Tetyana Beryozkina,Pavel Slepukhin,Vasiliy Bakulev |发布日期:2016.5
摘要:Highly Electrophilic 5-Azido-1-Methyl-4-Nitro-1H-Imidazole And Sulfonyl Azides Were Demonstrated To React With Alicyclic Amines And Cyclic Ketones In The Absence Of Any Catalyst Or Additive To Afford Novel N-(4-Nitroimidazol-5-Yl)- Or N-Sulfonylamidines Respectively. Based On Single Crystal X-Ray Analysis, A Revision Of The Previously Reported Data Of Gao And Co-Workers On The Direction Of The Reaction

合成参考文献


参考文献:10.1007/bf00478393
摘要:Novikov SS, Khmel'nitskii LI, Lebedev OV, Sevast'yanova VV, Epishina LV. Nitration of imidazoles with various nitrating agents. Chemistry of Heterocyclic Compounds. 1970 Apr;6(4):465–9. doi: 10.1007/bf00478393.
参考文献:10.1007/s10593-018-2389-5
摘要:Lian P, Guo X, Wang J, Chen L, Shen F. Nucleophilic substitution reactions of 1-methyl-4,5-dinitroimidazole with aqueous ammonia or sodium azide. Chemistry of Heterocyclic Compounds. 2018 Nov;54(11):1045–9. doi: 10.1007/s10593-018-2389-5.
参考文献:10.1007/s11178-005-0339-z
摘要:Titova IA, Vakul'skaya TI, Larina LI, Mizandrontsev MI, Volkov VA, Dolgushin GV, Lopyrev VA. Vicarious Nucleophilic C-Amination of Nitrobenzene and 5- and 6-Nitro-1-methylbenzimidazoles. Russian Journal of Organic Chemistry. 2005 Sep;41(9):1306–15. doi: 10.1007/s11178-005-0339-z.
参考文献:10.1007/bf00469932
摘要:Kochergin PM, Verenikina SG, Bushueva KS. Researches on imidazoles. Chemistry of Heterocyclic Compounds. 1965 Sep;1(5):519–21. doi: 10.1007/bf00469932.
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