6,8-dimethyl-3-(trifluoromethylsulfonyloxy)pyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione | 618881-14-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6,8-dimethyl-3-(trifluoromethylsulfonyloxy)pyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione
• 英文别名: (6,8-Dimethyl-5,7-dioxopyrimido[4,5-c]pyridazin-3-yl) trifluoromethanesulfonate；(6,8-dimethyl-5,7-dioxopyrimido[4,5-c]pyridazin-3-yl) trifluoromethanesulfonate
• CAS: 618881-14-4
• 化学式: C₉H₇F₃N₄O₅S
• 分子量: 340.24
• InChiKey: MIFHRDAEYVFVFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6,8-dimethyl-3-(trifluoromethylsulfonyloxy)pyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 10,12-Dimethyl-4-phenyl-3-propan-2-yl-3,7,8,10,12-pentazatricyclo[7.4.0.02,6]trideca-1(9),2(6),4,7-tetraene-11,13-dione
  参考文献：
  名称：

  摘要：

  Sonogashira cross-coupling of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with terminal alkynes afforded the corresponding 3-(alkyn-1-yl) derivatives. Oxidative amination of the latter compounds with primary alkylamines was accompanied by heterocyclization to give 6,8-dimethylpyrrolo[3',2':3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones.

  DOI：

  10.1023/a:1023431504814
• 作为产物：
  描述：

  6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 51.0h， 生成 6,8-dimethyl-3-(trifluoromethylsulfonyloxy)pyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione
  参考文献：
  名称：

  摘要：

  Sonogashira cross-coupling of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with terminal alkynes afforded the corresponding 3-(alkyn-1-yl) derivatives. Oxidative amination of the latter compounds with primary alkylamines was accompanied by heterocyclization to give 6,8-dimethylpyrrolo[3',2':3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones.

  DOI：

  10.1023/a:1023431504814

文献信息

• Oxidative alkylamination of azinones as a direct route to aminoazinones: study of some condensed diazinones
  作者：Anna V. Gulevskaya、Oleg N. Burov、Alexander F. Pozharskii、Mikhail E. Kletskii、Inna N. Korbukova

  DOI：10.1016/j.tet.2007.11.029

  日期：2008.1

  Oxidative alkylamination of azinones is a promising method for the preparation of a great variety of alkylaminoazinones. Treatment of 6,8-dimethyl-2-R-pyrimido[4,5-c]pyridazin-3,5,7(2H,6H,8H)-triones 7, 1,3-dimethyl-5-R-pteridin-2,4,6(1H,3H,6H)-triones 8 and 1,3,6-trimethylpyrimido[4,5-d]pyrimidin-2,4,7(1H,3H,6H)-trione 9 with alkylamine/AgPy2MnO4 or alkylamine/KMnO4 has been shown to produce their 4-, 7- and 5-alkylamino derivatives, respectively, in good yields. While 1-methylquinoxalin-2(1H)-one 10 is smoothly alkylaminated under the above conditions giving 3-alkylamino derivatives, quinoxaline itself does not take part in this reaction. Factors influencing oxidative alkylamination of azinones and a regioselectivity of the process are discussed. (C) 2007 Elsevier Ltd. All rights reserved.
• ——
  作者：V. V. Gorunenko

  DOI：10.1023/a:1023431504814

  日期：——

  Sonogashira cross-coupling of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with terminal alkynes afforded the corresponding 3-(alkyn-1-yl) derivatives. Oxidative amination of the latter compounds with primary alkylamines was accompanied by heterocyclization to give 6,8-dimethylpyrrolo[3',2':3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones.