9-(azidomethyl)-5H-pyrido[4,3-e]thiazolo[3,2-a]-pyrimidin-5-one | 1585169-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 9-(azidomethyl)-5H-pyrido[4,3-e]thiazolo[3,2-a]-pyrimidin-5-one
• CAS: 1585169-10-3
• 化学式: C₁₀H₆N₆OS
• 分子量: 258.263
• InChiKey: XYXFZXUYSINYSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.02
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9-(azidomethyl)-5H-pyrido[4,3-e]thiazolo[3,2-a]-pyrimidin-5-one 、 2-丙炔-1-醇 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以67%的产率得到9-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]-5Hpyrido[4,3-e]thiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Fused pyrimidine systems: XIII. Synthesis and some transformations of 1,3-thiazolo(thiazino)-fused pyrido[3,4-d]pyrimidines

  摘要：

  2-[Allyl(propargyl)sulfanyl]pyrido[3,4-d]pyrimidin-4-ones at heating in polyphosphoric acid undergo an intramolecular cyclization with the formation of pyrido[4,3-e]thiazolo-[3,2-a]pyrimidin-5-ones of angular structure. Under similar conditions the cyclization of 2-(cinnamylsulfanyl)pyrido[3,4-d]-pyrimidin-4-one results in a linear pyrido[3',4':4,5]pyrimido-[2,1-b][1,3]thiazin-6-one. The iodocyclization of the same substrates affords the corresponding 9-(iodomethyl)(iodomethylidene)pyrido[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-5-ones and 3-iodopyrido[3',4':4,5]pyrimido[2,1-b][1,3]thiazin-6-one of angular structure. 9-(Iodomethyl)-8,9-dihydro-5H-pyrido[4,3-e][1,3]thiazolo[3,2-a]pyrimidin-5-one treated with sodium azide gave 9-(azidomethyl) derivative whose cyclization with substituted alkynes in the presence of copper compounds provided pyrido [4,3-e][1,3]thiazolo[3,2-a]pyrimidinylmethyltriazoles.

  DOI：

  10.1134/s1070428014020201
• 作为产物：
  描述：

  9-(iodomethylene)-8,9-dihydro-5H-pyrido[4,3-e]-thiazolo[3,2-a]pyrimidin-5-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到9-(azidomethyl)-5H-pyrido[4,3-e]thiazolo[3,2-a]-pyrimidin-5-one
  参考文献：
  名称：

  Fused pyrimidine systems: XIII. Synthesis and some transformations of 1,3-thiazolo(thiazino)-fused pyrido[3,4-d]pyrimidines

  摘要：

  2-[Allyl(propargyl)sulfanyl]pyrido[3,4-d]pyrimidin-4-ones at heating in polyphosphoric acid undergo an intramolecular cyclization with the formation of pyrido[4,3-e]thiazolo-[3,2-a]pyrimidin-5-ones of angular structure. Under similar conditions the cyclization of 2-(cinnamylsulfanyl)pyrido[3,4-d]-pyrimidin-4-one results in a linear pyrido[3',4':4,5]pyrimido-[2,1-b][1,3]thiazin-6-one. The iodocyclization of the same substrates affords the corresponding 9-(iodomethyl)(iodomethylidene)pyrido[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-5-ones and 3-iodopyrido[3',4':4,5]pyrimido[2,1-b][1,3]thiazin-6-one of angular structure. 9-(Iodomethyl)-8,9-dihydro-5H-pyrido[4,3-e][1,3]thiazolo[3,2-a]pyrimidin-5-one treated with sodium azide gave 9-(azidomethyl) derivative whose cyclization with substituted alkynes in the presence of copper compounds provided pyrido [4,3-e][1,3]thiazolo[3,2-a]pyrimidinylmethyltriazoles.

  DOI：

  10.1134/s1070428014020201