7-(2-hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione | 1363156-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-(2-hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
• 英文别名: 7-(2-Hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4-dione；7-(2-hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4-dione
• CAS: 1363156-71-1
• 化学式: C₁₅H₁₂N₄O₅
• 分子量: 328.284
• InChiKey: IDBXQAUYWORTMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(2-hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  融合的3-硝基吡啶和其他硝基取代的杂芳烃的区域选择性直接芳构化：硝基基团作为指导基团的多用途性质。

  摘要：

  我们报道了一系列融合的3-硝基吡啶的Pd和Ni催化，导向和区域选择性的CH芳基化反应。此处描述的方法是用于药物样融合吡啶的化学功能化的简便工具。讨论了反应的范围和局限性，硝基的化学势以及可能的反应机理。

  DOI：

  10.1002/cctc.201402715
• 作为产物：
  描述：

  2'-Hydroxy-ω-nitroacetophenone 在 硫酸 、 溶剂黄146 作用下， 反应 10.0h， 生成 7-(2-hydroxyphenyl)-1,3-dimethyl-6-nitropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone

  摘要：

  3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal [3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.101

文献信息

• Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone
  作者：Viktor O. Iaroshenko、Satenik Mkrtchyan、Ashot Gevorgyan、Marcelo Vilches-Herrera、Dmitri V. Sevenard、Alexander Villinger、Tariel V. Ghochikyan、Ashot Saghiyan、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1016/j.tet.2011.06.101

  日期：2012.3

  3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal [3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.
• Regioselective Direct Arylation of Fused 3-Nitropyridines and Other Nitro-Substituted Heteroarenes: The Multipurpose Nature of the Nitro Group as a Directing Group
  作者：Viktor O. Iaroshenko、Ashot Gevorgyan、Satenik Mkrtchyan、Tatevik Grigoryan、Ester Movsisyan、Alexander Villinger、Peter Langer

  DOI：10.1002/cctc.201402715

  日期：2015.1

  We report Pd‐ and Ni‐catalysed, guided and regioselective CH arylations of a series of fused 3‐nitropyridines. The method described here is a facile tool for the chemical functionalisation of drug‐like fused pyridines. The scope and limitations of the reaction, the chemical potential of the nitro group and a putative reaction mechanism are discussed.

  我们报道了一系列融合的3-硝基吡啶的Pd和Ni催化，导向和区域选择性的CH芳基化反应。此处描述的方法是用于药物样融合吡啶的化学功能化的简便工具。讨论了反应的范围和局限性，硝基的化学势以及可能的反应机理。