1,3-dimethyl-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: 1,3-dimethyl-1H-pyrazolo<3,4-d>thiazole-5-carbonitrile
• 英文别名: 1,3-dimethyl-1H-pyrazolo[3,4-d]thiazole-5-carbonitrile；1,3-Dimethylpyrazolo[3,4-d][1,3]thiazole-5-carbonitrile
• 化学式: C₇H₆N₄S
• 分子量: 178.217
• InChiKey: BGLFNPVNQIRESU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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)-1,3-dimethyl-1H-pyrazol-5-amine 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 二苯醚 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 1,3-dimethyl-1H-pyrazolo<3,4-d>thiazole-5-carbonitrile
  参考文献：
  名称：

  Synthesis of Fused 1,2,4-Dithiazines and 1,2,3,5-Trithiazepines

  摘要：

  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%).

  DOI：

  10.1021/jo501881y

文献信息

• 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：——