tetrazolo[1,5-c]-pyrimidine | 274-88-4

• 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: tetrazolo[1,5-c]-pyrimidine
• 英文别名: Tetrazolo<1.5-c>pyrimidin；Tetrazolo<1.5-c>pyrimidin;4-Azido-pyrimidin；Tetrazolo[1,5-c]pyrimidine
• CAS: 274-88-4
• 化学式: C₄H₃N₅
• mdl: MFCD18449293
• 分子量: 121.101
• InChiKey: QGGITYBYHHFOHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrazolo[1,5-c]-pyrimidine 以 various solvent(s) 为溶剂， 反应 0.67h， 生成 1-氰基咪唑 、 (2-isocyanovinyl)carbodiimide
  参考文献：
  名称：

  2-Pyrazinylnitrene and 4-Pyrimidylnitrene. Ring Expansion to 1,3,5-Triazacyclohepta-1,2,4,6-tetraene and Ring Opening to (2-Isocyanovinyl)carbodiimide

  摘要：

  Tetrazolo[1,5-a]pyrazine/2-azidopyrazine 9T/9A undergo photolysis in Ar matrix at cryogenic temperatures to yield 1,3,5-triazacyclohepta-1,2,4,6-tetraene 21 as the first observable intermediate, and 1-cyanoimidazole 11 and (2-isocyanovinyl)carbodiimide 22 as the final products. The latter tautomerizes to 2-(isocyanovinyl)cyanamide 23 on warming to 40 K. The same intermediate 21 and the same final products are obtained on matrix photolysis of the isomeric tetrazolo[1,5-c]pyrimidine/4-azidopyrimidine 24T/24A. These photolysis results as well as those of the previously reported thermal ring contraction of N-15-labeled 2-pyrazinyl- and 4-pyrimidylnitrenes to 1-cyanoimidazoles can all be rationalized in terms of selective ring opening of 21 or nitrine 10 to a nitrile ylide zwitterion 28 prior to formation of the final products, 11 and 22. The results are supported by high-level ab initio and DFT calculations (CASPT2-CASSCF(6,6), G3(MP2), and B3LYP/6-31+G*) of the energies and IR spectra of the intermediates and products.

  DOI：

  10.1021/jo0256991

文献信息

• 2-Pyrazinylnitrene and 4-Pyrimidylnitrene. Ring Expansion to 1,3,5-Triazacyclohepta-1,2,4,6-tetraene and Ring Opening to (2-Isocyanovinyl)carbodiimide
  作者：Chris Addicott、Ming Wah Wong、Curt Wentrup

  DOI：10.1021/jo0256991

  日期：2002.11.1

  Tetrazolo[1,5-a]pyrazine/2-azidopyrazine 9T/9A undergo photolysis in Ar matrix at cryogenic temperatures to yield 1,3,5-triazacyclohepta-1,2,4,6-tetraene 21 as the first observable intermediate, and 1-cyanoimidazole 11 and (2-isocyanovinyl)carbodiimide 22 as the final products. The latter tautomerizes to 2-(isocyanovinyl)cyanamide 23 on warming to 40 K. The same intermediate 21 and the same final products are obtained on matrix photolysis of the isomeric tetrazolo[1,5-c]pyrimidine/4-azidopyrimidine 24T/24A. These photolysis results as well as those of the previously reported thermal ring contraction of N-15-labeled 2-pyrazinyl- and 4-pyrimidylnitrenes to 1-cyanoimidazoles can all be rationalized in terms of selective ring opening of 21 or nitrine 10 to a nitrile ylide zwitterion 28 prior to formation of the final products, 11 and 22. The results are supported by high-level ab initio and DFT calculations (CASPT2-CASSCF(6,6), G3(MP2), and B3LYP/6-31+G*) of the energies and IR spectra of the intermediates and products.

表征谱图