ethyl (1-phenyl-7-amino-5-oxo-1,2,4-triazolo[4,3-a]pyrimidin-3-yl)carboxylate | 407627-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl (1-phenyl-7-amino-5-oxo-1,2,4-triazolo[4,3-a]pyrimidin-3-yl)carboxylate
• 英文别名: 7-amino-3-ethoxycarbonyl-1-phenyl[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one；Ethyl 7-amino-5-oxo-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidine-3-carboxylate
• CAS: 407627-20-7
• 化学式: C₁₄H₁₃N₅O₃
• 分子量: 299.289
• InChiKey: MFLRDABEQAZBTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  424.8±48.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (1-phenyl-7-amino-5-oxo-1,2,4-triazolo[4,3-a]pyrimidin-3-yl)carboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 7-benzoylamino-3-ethoxycarbonyl-1-phenyl-pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5,6-(1H,8H)-dione
  参考文献：
  名称：

  A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione

  摘要：

  Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6(1H,8H)-diones.

  DOI：

  10.1007/s00706-002-0469-8
• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 、 ethyl (phenylhydrazono)chloroacetate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到ethyl (1-phenyl-7-amino-5-oxo-1,2,4-triazolo[4,3-a]pyrimidin-3-yl)carboxylate
  参考文献：
  名称：

  A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione

  摘要：

  Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6(1H,8H)-diones.

  DOI：

  10.1007/s00706-002-0469-8

文献信息

• Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents
  作者：Abdou Abdelhamid、Sobhi Gomha、Nadia Abdelriheem、Saher Kandeel

  DOI：10.3390/molecules21070929

  日期：——

  3-d]pyrimidin-4(1H)-ones, respectively. Also, hydrazonoyl halides were reacted with N’-(1-(1H-indol-3-yl)ethylidene)-2-cyanoacetohydrazide to afford 1,3,4-thiadiazole derivatives. Structures of the new synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Fifteen of the new compounds have been evaluated for their antitumor activity

  2-(3-(1H-Indol-3-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-取代-5-(取代二氮烯基)噻唑和2-(1H-indol-3-yl)-9-取代-4,7-二取代吡啶并[3,2-e][1,2,4]三唑并[4,3-a]嘧啶-5(7H) -ones 通过腙酰卤化物与 3-(1H-indol-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 和 7-(1H -indol-3-yl)-2-thioxo-5-取代的-2,3-二氢吡啶并[2,3-d]嘧啶-4(1H)-ones，分别。此外，腙酰卤与N'-(1-(1H-吲哚-3-基)亚乙基)-2-氰基乙酰肼反应得到1,3,4-噻二唑衍生物。新合成的结构是在元素分析、光谱数据和可能的替代合成路线的基础上阐明的。已经评估了 15 种新化合物对
• Multicomponent Synthesis of Novel Penta-Heterocyclic Ring Systems Incorporating a Benzopyranopyridine Scaffold
  作者：Sayed Riyadh、Sobhi Gomha

  DOI：10.1055/s-0033-1340085

  日期：——

  simple one-pot method is reported for the synthesis of several novel series of chromeno[4′,3′:4,5]pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-6,14-diones, chromeno[4′,3′:4,5]pyr­ido[2,3-d]thiazolo[3,2-a]pyrimidine-6,14-diones, and chrom-­eno[4′′,3′′:4′,5′]pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3]thiazine-6,15-dione by a multicomponent reaction of salicylaldehyde, ethyl acetoacetate, and the appropriate fused

  摘要 报道了一种简单的一锅法，用于合成几个新系列的chromeno [4'，3'：4,5] pyrido [2,3- d ] [1,2,4] triazolo [4,3- a ] pyrimidine-6,14-diones，chromeno [4'，3'：4,5] pyrido [2,3- d ] thiazolo [3,2 - a ] pyrimidine-6,14-diones和chrom-eno [通过多组分反应4''，3''：4'，5'] pyrido [2'，3'：4,5] pyrimido [2,1- b ] [1,3]噻嗪-6,15-二酮回流冰醋酸中的水杨醛，乙酰乙酸乙酯和适当的稠合杂环胺 通过光谱和元素分析确定了新合成化合物的结构。阐明了单步反应的机理。 报道了一种简单的一锅法，用于合成几个新系列的chromeno [4'，3'：4,5] pyrido [2,3- d ]
• Novel synthesis of 1,2,4-triazolo[4,3- a ]pyrimidin-5-one derivatives
  作者：Hamdi M Hassaneen、Hyam A Abdelhadi、Tayseer A Abdallah

  DOI：10.1016/s0040-4020(01)01026-2

  日期：2001.12

  1,2-Dihydro-2-thioxopyrimidin-4(3H)ones 6 react with C-ethoxycarbonyl-N-arylhydrazonoyl chlorides 1 to give 1,2,4-triazolo[4,3-a] pyrimidines 11 in good yield. The latter products 11 react with benzenediazonium chloride, nitrous acid, acetyl chloride and chloroacetyl chloride to give the corresponding substitution products 16-18. The structures of the newly synthesized compounds are established on the basis of chemical and spectroscopic evidence. (C) 2001 Published by Elsevier Science Ltd.
• Cellulose Sulfuric Acid as an Eco-Friendly Catalyst for Novel Synthesis of Pyrido[2,3-<i>d</i>][1,2,4]triazolo[4,3-<i>a</i>]pyrimidin-5-ones
  作者：Sobhi M. Gomha、Sayed M. Riyadh

  DOI：10.5935/0103-5053.20150052

  日期：——

  A novel synthesis of a series of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones has been developed from reactions of 1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-3-arylprop-2-en-1-ones and 7-amino-1,3-disubstituted[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones in dioxane under thermal conditions, using cellulose sulfuric acid as an eco-friendly acid catalyst. The reaction mechanism was proposed and the structures of the newly synthesized compounds were established on the basis of spectral data (mass spectrometry, infrared, H-1 and C-13 nuclear magnetic resonance) and elemental analyses.
• A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione
  作者：Mosselhi A. N. Mosselhi

  DOI：10.1007/s00706-002-0469-8

  日期：2002.9.1

  Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6(1H,8H)-diones.