pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thione | 374073-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thione
• 英文别名: 5-Sulfanylidene-3,4,6,7,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,10,12-tetraen-8-one
• CAS: 374073-99-1
• 化学式: C₈H₅N₅OS
• 分子量: 219.227
• InChiKey: CNINZUCQJXKIFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thione 在 四丁基氢氧化铵 、 silica gel 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.33h， 生成 5-methyl-3-methylthiopyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one
  参考文献：
  名称：

  Preparative and theoretical study on chain length-dependence and substrate selectivity in the cycloalkylation of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones

  摘要：

  Cyclization of condensed [1,2,4]triazolo[4,3-b]pyridazine-3(2H)-6(5H)-ones with alpha,omega-dibromoalkanes afforded a series of novel ring systems including zwitterions and isomeric tetracyclic lactams. The product distribution is controlled by the chain-length of the reagent, the polarity of the solvent and the structure of ring A in the substrate. The observed substrate selectivity was interpreted on the basis of amide-I IR frequencies and by the results of ab initio B3LYP DFr calculations carried out at 6-31 G and 6-31 G(d) basis sets using IPCM solvation model. The cycloalkylation with 1,4-dibromobutane gave also macrocyles as detectable by-products which underwent ring contraction yielding lactams on attempted chromatographic separation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01156-0
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 8-hydrazinopyrido[2,3-d]pyridazine-5(6H)-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以79%的产率得到pyrido[2,3-d][1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thione
  参考文献：
  名称：

  Novel ring transformations of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones effected by dialkyl-acetylenedicarboxylates

  摘要：

  On heating with dialkyl-acetylenedicarboxylates in DMF condensed [1,2,4]-triazolo[4,3-b] pyridazine-6(5H)-one-3(2H)-thiones undergo unprecedented ring transformations yielding novel tetracyclic 1,3-diazepines and thiazolotriazole derivatives depending on the applied reaction temperature. The observed substrate selectivity was interpreted on the basis of the results of comparative theoretical calculations carried out at semiempirical level (AMI). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00672-x

文献信息

• Preparative and theoretical study on chain length-dependence and substrate selectivity in the cycloalkylation of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones
  作者：Antal Csámpai、Mónika Simó、Zoltán Szlávik、András Kotschy、Gábor Magyarfalvi、György Túrós

  DOI：10.1016/s0040-4020(02)01156-0

  日期：2002.10

  Cyclization of condensed [1,2,4]triazolo[4,3-b]pyridazine-3(2H)-6(5H)-ones with alpha,omega-dibromoalkanes afforded a series of novel ring systems including zwitterions and isomeric tetracyclic lactams. The product distribution is controlled by the chain-length of the reagent, the polarity of the solvent and the structure of ring A in the substrate. The observed substrate selectivity was interpreted on the basis of amide-I IR frequencies and by the results of ab initio B3LYP DFr calculations carried out at 6-31 G and 6-31 G(d) basis sets using IPCM solvation model. The cycloalkylation with 1,4-dibromobutane gave also macrocyles as detectable by-products which underwent ring contraction yielding lactams on attempted chromatographic separation. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Novel ring transformations of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones effected by dialkyl-acetylenedicarboxylates
  作者：Mónika Simó、Antal Csámpai、Veronika Harmat、Orsolya Barabás、Gábor Magyarfalvy

  DOI：10.1016/s0040-4020(01)00672-x

  日期：2001.8

  On heating with dialkyl-acetylenedicarboxylates in DMF condensed [1,2,4]-triazolo[4,3-b] pyridazine-6(5H)-one-3(2H)-thiones undergo unprecedented ring transformations yielding novel tetracyclic 1,3-diazepines and thiazolotriazole derivatives depending on the applied reaction temperature. The observed substrate selectivity was interpreted on the basis of the results of comparative theoretical calculations carried out at semiempirical level (AMI). (C) 2001 Elsevier Science Ltd. All rights reserved.