4-amino-N-methyl-1H-imidazole-5-carboxamide;hydrochloride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-amino-N-methyl-1H-imidazole-5-carboxamide;hydrochloride
• 化学式: C₅H₈N₄O*ClH
• 分子量: 176.606
• InChiKey: MKLVYHYFDRFXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.8
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-N-methyl-1H-imidazole-5-carboxamide;hydrochloride 在 盐酸 、 sodium nitrite 作用下， 生成 5-diazoimidazole-4-(N-methylcarboxamide)
  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
• 作为产物：
  描述：

  5-Nitro-imidazol-4-(N-methyl)-carboxamid 、 氯化亚锡 以61%的产率得到
  参考文献：
  名称：

  PUSHKAREVA Z. V.; OFITSEROV V. I.; MOKRUSHIN V. S.; AGLITSKAYA K. V., XIMIYA GETEROTSIKL. SOEDIN. , 1975, HO 8, 1141-1145

  摘要：

  DOI：

文献信息

• Synthesis of imidazolyl dithiocarbamates and their reactions with phenacyl bromides
  作者：O. S. El’tsov、V. S. Mokrushin、M. V. Smirnova、M. Z. Shafikov

  DOI：10.1007/s11172-011-0138-3

  日期：2011.5

  The reactions of ethyl (5-carbamoyl-3H-imidazol-4-yl)dithiocarbamate with phenacyl bromides afford the S-alkylation products as a mixture of E/Z-isomers, which undergo cyclization to 5-(2-oxo-4-arylthiazol-3-yl)-1H-imidazole-4-carboxamides under the action of a base.

  (5-氨基甲酰基-3H-咪唑-4-基)二硫代氨基甲酸乙酯与苯甲酰溴反应得到S-烷基化产物，为E/Z-异构体的混合物，其环化为5-(2-oxo-4-芳基噻唑-3-基)-1H-咪唑-4-甲酰胺在碱作用下。
• Synthesis of novel derivatives of 2-(azolylimino)thiazoline
  作者：O. S. Eltsov、V. S. Mokrushin、A. V. Tkachev

  DOI：10.1007/s11172-005-0116-8

  日期：2004.10

  Successive alkylation of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with alkyl halides and chloroacetone gave (N-oxopropylimidazolyl)isothioureas, which were easily converted into derivatives of purine and imidazopyrazinone. In the case of ethyl 5-(3-phenylthioureido)-3H-imidazole-4-carboxylate, primary alkylation occurs at the N atom of the imidazole ring. Reactions of 5-(3-phenylthiourei

  5-(3-苯基硫脲基)-3H-咪唑-4-甲酰胺与卤代烷和氯丙酮的连续烷基化得到(N-氧代丙基咪唑基)异硫脲，其很容易转化为嘌呤和咪唑并吡嗪酮的衍生物。在 5-(3-苯基硫脲基)-3H-咪唑-4-羧酸乙酯的情况下，初级烷基化发生在咪唑环的 N 原子上。5-(3-苯基硫脲基)-3H-咪唑-4-甲酰胺与卤代酮反应得到许多4-羟基-2-咪唑基亚胺噻唑烷和2-咪唑基亚氨基-Δ4-噻唑啉。
• Heterocyclization of dithiocarbamates and thioureas of the imidazole series with dimethylacetylenedicarboxylate
  作者：Oleg S. Eltsov、Elena A. Kamalova、Vladimir S. Mokrushin

  DOI：10.1070/mc2006v016n01abeh002225

  日期：2006.1

  A heterocyclic system of imidazo[1,5-c][1,3,5]thiadiazine was synthesised by the interaction of polyfunctional imidazolyl thioureas and ethyldithiocarbamates with dimethylacetylenedicarboxylate.