3-Phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile | 74414-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile
• 英文别名: 3-Phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-carbonitrile；3-phenyltriazolo[4,5-d]pyrimidine-7-carbonitrile
• CAS: 74414-82-7
• 化学式: C₁₁H₆N₆
• 分子量: 222.209
• InChiKey: XRWNNIXSKNHOMN-UHFFFAOYSA-N

物化性质

• 熔点：
  166-167 °C
• 沸点：
  463.5±48.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile 在 盐酸羟胺 、 potassium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.0h， 以96%的产率得到3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carboxamidoxime
  参考文献：
  名称：

  Higashino, Takeo; Katori, Tatsuhiko; Yoshida, Shizuo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 255 - 261

  摘要：

  DOI：
• 作为产物：
  描述：

  7-chloro-3-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine 、 氰化钾 在 sodium 4-methylbenzenesulfinate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以68%的产率得到3-Phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile
  参考文献：
  名称：

  Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

  摘要：

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.

  DOI：

  10.3987/com-94-s(b)38

文献信息

• Triazolo(4,5-d)pyrimidines. XII. Reactions of 6-Benzoyl-6,7-dihydro-3-phenyl-3H-1,2,3-triazolo(4,5-d)pyrimidines(Triazolopyrimidine Reissert Compounds) with Acid, Base, and Electrophile.
  作者：Ken-ichi TANJI、Susumu SATO、Yoshihiko KANAMARU、Chihoko IIJIMA、Akira MIYASHITA、Takeo HIGASHINO

  DOI：10.1248/cpb.40.513

  日期：——

  In the treatment of 6-benzoyl-6, 7-dihydro-3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidine-7-carbonitrile (1, triazolo-pyrimidine Reissert compound) and 6-benzoyl-6, 7-dihydro-5-methyl-3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidine-7-carbonitrile (2, 5-methyltriazolopyrimidine Reissert compound) with an acid, the ring fission of the pyrimidine ring proceeded to give the triazole derivatives (3-7). Alkaline hydrolysis of 2 and 1 gave 5-metyl-3-phenyl- (10) and 3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidines (9), respectively. The anions, generated from 1 and 2 with sodium hydride (NaH), underwent aromatization to give the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidine-7-carbonitriles (12 and 14). Compounds 1 and 2 reacted with arylaldehydes in the presence of NaH to give corresponding 3H-1, 2, 3-triazolo[4, 5-d]pyrimidin-7-ylmethyl benzoates (15 and 17).

  在用酸处理6-苯甲酰基-6, 7-二氢-3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶-7-腈（1，三唑嘧啶Reissert化合物）和6-苯甲酰基-6, 7-二氢-5-甲基-3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶-7-腈（2，5-甲基三唑嘧啶Reissert化合物）时，嘧啶环开环反应得到了三唑衍生物（3-7）。2和1的碱水解分别得到了5-甲基-3-苯基-（10）和3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶（9）。由1和2与氢化钠（NaH）生成的阴离子发生了芳构化，得到了3H-1, 2, 3-三唑并[4, 5-d]嘧啶-7-腈（12和14）。化合物1和2在NaH存在下与芳香醛反应，得到了相应的3H-1, 2, 3-三唑并[4, 5-d]嘧啶-7-基甲基苯甲酸酯（15和17）。
• Ring transformation of condensed pyrimidines by enamines and ynamines. Formation of condensed pyridines and condensed diazocines.
  作者：Akira MIYASHITA、Naokata TAIDO、Susumu SATO、Ken-ichi YAMAMOTO、Hitoshi ISHIDA、Takeo HIGASHINO

  DOI：10.1248/cpb.39.282

  日期：——

  A [4+2]-cycloaddition of quinazoline (2) and the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidine 4 with enamines 1a-e resulted in ring transformation into the quinolines, 3a and 3c, and the 3H-1, 2, 3-triazolo[4, 5-b]pyridines, 5a-e, respectively. Similarly, the ynamine 13a cycloadded to 2 and its 4-cyano derivative 6, giving the quinolines, 14a and 14b, respectively.On the other hand, the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 4, 15, 8, 16, 17, 18, and 19 underwent [2+2]-cycloaddition with the ynamine 13a, resulting in ring transformation into the corresponding 3H-1, 2, 3-triazolo[4, 5-d]-[1, 3]diazocines 21a-27. The 7-methoxy derivative 20, the 4-methoxy- and 4-cyano-1H-pyrazolo[3, 4-d]pyrimidines, 30 and 31, and the 6-cyano-9H-purine 36 also underwent [2+2]-cycloaddition with 13a to give the corresponding 3H-1, 2-3-triazolo[4, 5-b][1, 5]diazocine 28, 1H-pyrazolo[3, 4-b][1, 5]diazocines, 32 and 33, and 3H-imidazo[4, 5-b]-[1, 5]diazocine 37, respectively.The structures of the 1, 3- and 1, 5-diazocines, 21a and 28, were determined by X-ray crystallography.

  喹唑啉（2）和3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4）与烯胺（1a-e）进行[4+2]环加成反应，导致环转化为喹啉（3a和3c）和相应的3H-1, 2, 3-三氮杂[4, 5-b]吡啶（5a-e）。类似地，烯氨（13a）与2及其4-氰基衍生物6进行环加成，分别生成喹啉（14a和14b）。另一方面，3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4、15、8、16、17、18和19）与烯氨（13a）发生[2+2]环加成反应，导致环转化为相应的3H-1, 2, 3-三氮杂[4, 5-d]-[1, 3]二氮环（21a-27）。7-甲氧基衍生物20、4-甲氧基和4-氰基的1H-吡唑[3, 4-d]嘧啶（30和31）以及6-氰基-9H-嘌呤（36）也与13a发生[2+2]环加成，分别生成相应的3H-1, 2-3-三氮杂[4, 5-b][1, 5]二氮环（28）、1H-吡唑[3, 4-b][1, 5]二氮环（32和33）和3H-咪唑[4, 5-b]-[1, 5]二氮环（37）。1, 3-和1, 5-二氮环（21a和28）的结构通过X射线晶体学确定。
• Higashino, Takeo; Katori, Tatsuhiko; Kawaraya, Hideji, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 337 - 343
  作者：Higashino, Takeo、Katori, Tatsuhiko、Kawaraya, Hideji、Hayashi, Eisaku

  DOI：——

  日期：——
• Higashino, Takeo; Hayashi, Eisaku; Matsuda, Hideaki, Heterocycles, 1981, vol. 15, # 1, p. 483 - 487
  作者：Higashino, Takeo、Hayashi, Eisaku、Matsuda, Hideaki、Katori, Tatsuhiko

  DOI：——

  日期：——
• HIGASHINO T.; KATORI T.; KAWARAYA H.; HAYASHI E., CHEM. AND PHARM. BULL., 1980, 28, NO 1, 337-343
  作者：HIGASHINO T.、 KATORI T.、 KAWARAYA H.、 HAYASHI E.

  DOI：——

  日期：——