7,8,9,10-tetrahydro-s-triazolo<3,4-a>phthalazine | 73075-03-3

• 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: 7,8,9,10-tetrahydro-s-triazolo<3,4-a>phthalazine
• 英文别名: 7,8,9,10-tetrahydro-[1,2,4]triazolo[3,4-a]phthalazine；7,8,9,10-Tetrahydro-s-triazolo<3,4-a>phthalazin；7,8,9,10-Tetrahydro-[1,2,4]triazolo[3,4-a]phthalazine
• CAS: 73075-03-3
• 化学式: C₉H₁₀N₄
• 分子量: 174.205
• InChiKey: AFDDHKHSFWORGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [1,2,4]Triazolo[4,3-b]pyridazine 反应 14.0h， 生成 7,8,9,10-tetrahydro-s-triazolo<3,4-a>phthalazine
  参考文献：
  名称：

  Photoalkylation of s-triazolo[4,3-b]pyridazine with alcohols and glycols

  摘要：

  DOI：

  10.1021/jo01300a011

文献信息

• [EN] REGIO-SELECTIVE SYNTHESIS OF IMIDAZO[1,2-A]PYRIMIDINES<br/>[FR] SYNTHÈSE RÉGIO-SÉLECTIVE D'IMIDAZO[1,2-A]PYRIMIDINES
  申请人：GENENTECH INC

  公开号：WO2020227576A1

  公开（公告）日：2020-11-12

  A method of regio-selectively synthesizing an imidazo-pyrimidine compound of formulae (XXa) or (XXb) comprising a step of coupling a first compound of formula XX-P1a or XX-P1b with a second compound of formula XX-P2. This annulation reaction between β-ethoxy acrylamides and phosphorylated aminoimidazoles to furnish imidazo[1,2-a]pyrimidin-amines relies on steering effects from endocyclic and exocyclic phosphorylated aminoimidazoles. The reaction furnishes either 2-amino or 4-amino constitutional isomers of imidazo[1,2-a]pyrimidines with good yields and ranges of 90:10 – 99:1 regio-selectivity. The reaction is useful in the synthesis of various tracer molecules used in the study of neurological conditions such as where R3 and R4 together with the imidazole ring atoms to which they are bonded form a phenyl ring and the products are substituted benzimidazopyrimidines. The reaction can be generalized to form imidazo[1,2-a]pyrimidines substituted at either of their 2- and 4- positions by alkoxy or thioalkyl groups.

  一种选择性区域合成式（XXa）或（XXb）的咪唑嘧啶化合物的方法，包括将式XX-P1a或XX-P1b的第一化合物与式XX-P2的第二化合物偶联的步骤。这种β-乙氧基丙烯酰胺和磷酸化氨基咪唑之间的环化反应，用于合成咪唑[1,2-a]嘧啶胺，依赖于内环和外环磷酸化氨基咪唑的导向效应。该反应以良好的产率提供咪唑[1,2-a]嘧啶的2-氨基或4-氨基构型异构体，并具有90:10至99:1的选择性。该反应在合成用于研究神经系统疾病的各种示踪分子中很有用，例如当R3和R4与它们结合的咪唑环原子形成苯环时，产物为取代苯基咪唑嘧啶。该反应可推广为在其2-位和4-位之一被烷氧基或硫代烷基基团取代的咪唑[1,2-a]嘧啶。
• 3,6,7,8-Substituted-s-triazolo(4,3-b)-pyridazines, their preparation and compositions comprising them
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0029130A1

  公开（公告）日：1981-05-27

  3,6,7,8-substituted-s-triazolo-pyridazine compounds of the formula wherein R3 represents hydrogen or loweralkyl, R6 represents amino, loweralkylamino, diloweralkylamino, heterocyclic amino or lower alkyl substituted heterocyclic amino, wherein the heterocyclic moiety forms a 5, 6 or 7 membered ring, having one or two ring nitrogen atoms and zero or one ring sulfur or oxygen atom; T7 represents loweralkyl; R8 represents hydrogen or loweralkyl; or R7 and R8 taken together represent polymethylene of 3 or 4 methylene units or polymethylene substituted by lower alkyl, or methano or ethano bridges; and their pharmacologically acceptable salts are made by reacting a carboxylic acid with a substituted 3-hydrazino-6-halo-pyridazine and then reacting the resulting 6-halotriazolopyridazine with a corresponding base. The compounds have pharmacological activity as bronchodilators.

  式中，R3代表氢或低碳基，R6代表氨基，低碳基氨基，二低碳基氨基，杂环氨基或低碳基取代的杂环氨基，其中杂环基形成一个5、6或7个成员的环，有一个或两个环氮原子和零或一个环硫或氧原子；T7代表低碳基；R8代表氢或低碳基；或R7和R8一起代表3或4个亚甲基单元的聚甲基或低碳基取代的聚甲基，或甲烷或乙烷桥；它们的药物学可接受盐是由羧酸与取代的3-肼基-6-卤代吡啶嗪反应，然后将得到的6-卤代三唑吡啶与相应的碱反应制得的。这些化合物具有支气管扩张剂的药理活性。
• Regio-selective synthesis of imidazo[1,2-a]pyrimidines
  申请人：Genentech, Inc.

  公开号：US11325912B2

  公开（公告）日：2022-05-10

  A method of regio-selectively synthesizing an imidazo-pyrimidine compound of formulae (XXa) or (XXb) comprising a step of coupling a first compound of formula XX-P1a or XX-P1b with a second compound of formula XX-P2 This annulation reaction between β-ethoxy acrylamides and phosphorylated aminoimidazoles to furnish imidazo[1,2-a]pyrimidin-amines relies on steering effects from endocyclic and exocyclic phosphorylated aminoimidazoles. The reaction furnishes either 2-amino or 4-amino constitutional isomers of imidazo[1,2-a]pyrimidines with good yields and ranges of 90:10-99:1 regio-selectivity. The reaction is useful in the synthesis of various tracer molecules used in the study of neurological conditions such as where R3 and R4 together with the imidazole ring atoms to which they are bonded form a phenyl ring and the products are substituted benzimidazopyrimidines. The reaction can be generalized to form imidazo[1,2-a]pyrimidines substituted at either of their 2- and 4-positions by alkoxy or thioalkyl groups.

  一种选择性地合成式(XXa)或(XXb)咪唑嘧啶化合物的方法 包括将式 XX-P1a 或 XX-P1b 的第一种化合物与式 XX-P2 的第二种化合物偶联的步骤 β-乙氧基丙烯酰胺与磷酸化氨基咪唑之间的环化反应生成咪唑并[1,2-a]嘧啶胺依赖于内环和外环磷酸化氨基咪唑的转向效应。该反应可生成咪唑并[1,2-a]嘧啶的 2-氨基或 4-氨基构型异构体，产率高，区域选择性范围为 90:10-99:1。该反应可用于合成用于研究神经系统疾病的各种示踪分子，如 R3 和 R4 与它们所结合的咪唑环原子一起形成一个苯基环，而产物则是取代的苯并咪唑嘧啶。该反应可以推广到在咪唑并[1,2-a]嘧啶的 2 位和 4 位上形成被烷氧基或硫代烷基取代的咪唑并[1,2-a]嘧啶。
• BAJWA J. S.; SYKES P. J., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 12, 3085-3094
  作者：BAJWA J. S.、 SYKES P. J.

  DOI：——

  日期：——
• BOWN D. H.; BRADSHAW J. S., J. ORG. CHEM., 1980, 45, NO 12, 2320-2324
  作者：BOWN D. H.、 BRADSHAW J. S.

  DOI：——

  日期：——