3-methyl-1-phenyl-1H-pyrazolo<3,4-d>thiazole-5-carbonitrile

• 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-methyl-1-phenyl-1H-pyrazolo<3,4-d>thiazole-5-carbonitrile
• 英文别名: 3-methyl-1-phenyl-1H-pyrazolo[3,4-d]thiazole-5-carbonitrile；3-Methyl-1-phenylpyrazolo[3,4-d][1,3]thiazole-5-carbonitrile
• 化学式: C₁₂H₈N₄S
• 分子量: 240.288
• InChiKey: YTFZDXUVDUIKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5-amine 以83%的产率得到3-methyl-1-phenyl-1H-pyrazolo<3,4-d>thiazole-5-carbonitrile
  参考文献：
  名称：

  重新研究1 H-吡唑-5-胺与4,5-二氯1,2,3-二噻唑鎓氯化物的反应：一条通往吡唑并[3,4- c ]异噻唑和吡唑并[3,4- d ]噻唑的途径

  摘要：

  Appel盐1与1 H-吡唑-5-胺2的反应生成主要产物N-（4-氯-5 H -1,2,3-二噻唑-5-亚烷基）-1 H-吡唑-5-胺3和6 H-吡唑并[3,4- c ]异噻唑-3-腈5以及几种次要副产物。当吡唑被N-1甲基化时，可以通过调节反应介质的pH来改变3：5的产物比例：酸性条件有利于二噻唑基3的形成，而碱性条件有利于吡唑并[3,4- c]异噻唑5。此外，对N-（4-氯-5 H -1,2,3-二噻唑-5-亚烷基）-1 H-吡唑-5-胺3进行热解得到1 H-吡唑并[3,4- d ]噻唑- 5-腈4。单晶X射线晶体学支持4,6-二甲基-6 H-吡唑并[3,4- c ]异噻唑-3-甲腈（5a）的结构，并有助于解决先前错误的1 H-吡唑并[3]的结构分配。，4 - d ]噻唑-5-腈4。

  DOI：

  10.1021/jo500509e

文献信息

• Synthesis of Fused 1,2,4-Dithiazines and 1,2,3,5-Trithiazepines
  作者：Maria Koyioni、Maria Manoli、Panayiotis A. Koutentis

  DOI：10.1021/jo501881y

  日期：2014.10.17

  Reacting (Z)-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 5 with Et2NH and then with concd H2SO4 gives 5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitriles 7 in good yields (74-85%) and 6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitriles 9 as minor products (0-6%). Furthermore, the 1,3-dimethylpyrazole analogue 5a was transformed into the dithiazine 7a in two discrete steps, allowing the isolation of a disulfide intermediate (Z)-2-[(diethylamino)disulfan-yl]-2-[(1H-pyrazol-5-yl)imino]acetonitrile (8a). The one-pot, two-step reaction also worked with electron-rich hydroxy- and methoxy-substituted anilines. Thermolysis of the pyrazolo[3,4-e][1,2,4]dithiazines 7 gave the ring-contracted 1H-pyrazolo[3,4-d]thiazole-5-carbonitriles 6 (94-100%). With active sulfur, 1,3-dimethyl-5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitrile (7a) gave 1,3-dimethyl-6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitrile (9a), but on prolonged reaction times, it gave 5,7-dimethyl-5H-[1,2,3]dithiazolo[4,5-b]pyrazolo[3,4-e][1,4]thiazine (13). Finally, in the absence of acid, heating a solution of (Z)-2-[(diethylamino)disulfanyl]-2-[(1,3-dimethyl-1H-pyrazol-5-yl)imino]acetonitrile (8a) gave 4,6,10,12-tetramethyl-6H-pyrazolo[3,4-f]pyrazolo[3',4':4,5]pyrimido[6,1-d][1,2,3,5]trithiazepine-8,12b(10H)-dicarbonitrile (19) (67%).
• L'abbe, Gerrit; D'hooge, Bart; Dehaen, Wim, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2379 - 2380
  作者：L'abbe, Gerrit、D'hooge, Bart、Dehaen, Wim

  DOI：——

  日期：——