ethyl 7-{[2-azido-5-(ethoxycarbonyl)pyrimidin-4-yl]-methyl}-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 7-{[2-azido-5-(ethoxycarbonyl)pyrimidin-4-yl]-methyl}-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 7-{[2-azido-5-(ethoxycarbonyl)pyrimidin-4-yl]methyl}-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate；Ethyl 7-{[2-azido-5-(ethoxycarbonyl)pyrimidin-4-yl]methyl}-5-methyl-4,7-dihydrotetrazolo[1,5-a]-pyrimidine-6-carboxylate；ethyl 7-[(2-azido-5-ethoxycarbonylpyrimidin-4-yl)methyl]-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• 化学式: C₁₆H₁₈N₁₀O₄
• 分子量: 414.384
• InChiKey: MOWNAONNJNSINY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  ethyl 2-azido-4-methylpyrimidine-5-carboxylate 反应 288.0h， 以86%的产率得到ethyl 7-{[2-azido-5-(ethoxycarbonyl)pyrimidin-4-yl]-methyl}-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

  摘要：

  2-乙氧甲基亚甲基-3-酮基酯及其类似物与5-氨基四唑的相互作用是一种有效的合成新型氮杂环化合物的方法。带有烷基取代基的2-乙氧甲基亚甲基-3-酮基酯与5-氨基四唑反应，形成乙酰基2-氮杂嘧啶-5-羧酸酯，这些化合物能够进行进一步的亲核取代反应。在此反应中使用二乙酰乙二酯，可以得到乙酰基7-羟基四唑并环[1,5-a]嘧啶-6-羧酸乙酯，而使用乙酸乙酯基2-乙氧甲基亚甲基丙烯酸酯，则通过另一种途径生成5-[2,6-二氨基-3,5-双(乙氧羰基)吡啶-1-基]四唑-1-化物。乙酰基2-苯甲酰基-3-乙氧基丙烯酸酯通过两种反应途径与5-氨基四唑反应，形成乙酰基2-苯甲酰基-3-(1H-四唑-5-基)丙烯酸酯和乙酯基7-(1-乙氧基-1,3-二氧杂环戊烷-3-苯基丙基)-5-苯基-4,7-二氢四唑并环[1,5-a]嘧啶-6-羧酸乙酯。

  DOI：

  10.3762/bjoc.11.44

文献信息

• Reaction of 2-(ethoxymethylidene)-3-oxo carboxylic acid esters with tetrazol-5-amine
  作者：M. V. Goryaeva、Ya. V. Burgart、M. A. Ezhikova、M. I. Kodess、V. I. Saloutin

  DOI：10.1134/s1070428015070179

  日期：2015.7

  2-(Ethoxymethylidene)-3-oxo carboxylic acid esters reacted with tetrazol-5-amine to give ethyl 4-alkyl-2-azidopyrimidine-5-carboxylates capable of undergoing subsequent nucleophilic substitution of hydrogen on C-6 or azido group. The reaction of ethyl 2-benzoyl-3-ethoxyprop-2-enoate with tetrazol-5-amine was accompanied by partial decomposition to afford a mixture of ethyl 3-oxo-3-phenylpropanoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate. Ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate was formed as a result of cyclization of diethyl 2-(ethoxymethylidene)propanedioate with tetrazol-5-amine.
• The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
  作者：Marina V Goryaeva、Yanina V Burgart、Marina A Ezhikova、Mikhail I Kodess、Viktor I Saloutin

  DOI：10.3762/bjoc.11.44

  日期：——

  The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

  2-乙氧甲基亚甲基-3-酮基酯及其类似物与5-氨基四唑的相互作用是一种有效的合成新型氮杂环化合物的方法。带有烷基取代基的2-乙氧甲基亚甲基-3-酮基酯与5-氨基四唑反应，形成乙酰基2-氮杂嘧啶-5-羧酸酯，这些化合物能够进行进一步的亲核取代反应。在此反应中使用二乙酰乙二酯，可以得到乙酰基7-羟基四唑并环[1,5-a]嘧啶-6-羧酸乙酯，而使用乙酸乙酯基2-乙氧甲基亚甲基丙烯酸酯，则通过另一种途径生成5-[2,6-二氨基-3,5-双(乙氧羰基)吡啶-1-基]四唑-1-化物。乙酰基2-苯甲酰基-3-乙氧基丙烯酸酯通过两种反应途径与5-氨基四唑反应，形成乙酰基2-苯甲酰基-3-(1H-四唑-5-基)丙烯酸酯和乙酯基7-(1-乙氧基-1,3-二氧杂环戊烷-3-苯基丙基)-5-苯基-4,7-二氢四唑并环[1,5-a]嘧啶-6-羧酸乙酯。