N²,N²-dimethyl-thiazole-2,4-diamine | 75116-62-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N²,N²-dimethyl-thiazole-2,4-diamine
• 英文别名: 2-(N,N-Dimethylamino)-4-aminothiazol；2,4-Thiazolediamine, N2,N2-dimethyl-；2-N,2-N-dimethyl-1,3-thiazole-2,4-diamine
• CAS: 75116-62-0
• 化学式: C₅H₉N₃S
• 分子量: 143.213
• InChiKey: YGNAWCMPWLXVSX-UHFFFAOYSA-N

物化性质

• 沸点：
  260.2±32.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²,N²-dimethyl-thiazole-2,4-diamine 、 nitromalondialdehyde sodium salt 在 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 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

文献信息

• 3-(Dichloroacetyl)chromone; A New Building Block for the Synthesis of Formylated Purine Isosteres: Design and Synthesis of Fused α-(Formyl)pyridines
  作者：Viktor Iaroshenko、Peter Langer、Satenik Mkrtchyan、Gagik Ghazaryan、Ani Hakobyan、Aneela Maalik、Linda Supe、Alexander Villinger、Andrei Tolmachev、Dmytro Ostrovskyi、Vyacheslav Sosnovskikh、Tariel Ghochikyan

  DOI：10.1055/s-0030-1258364

  日期：2011.2

  The first synthesis of 3-(dichloroacetyl)chromone from 3-(dimethylamino)-1-(2-hydroxyphenyl)propen-1-one and dichloroacetyl chloride is described. The reaction of electron-rich aminoheterocycles with 3-(dichloroacetyl)chromone provides a set of diverse fused pyridines bearing the CHCl2-substituent at the α-position of the pyridine core. Subsequent hydrolysis leads to the formation of annulated α-(formyl)pyridines

  描述了由3-（二甲基氨基）-1-（2-羟基苯基）丙烯-1-酮和二氯乙酰氯首次合成3-（二氯乙酰基）色酮。富电子的氨基杂环与3-（二氯乙酰基）色酮的反应提供了一组不同的稠合吡啶，其在吡啶核的α-位带有CHCl 2-取代基。随后的水解导致环状的α-（甲酰基）吡啶的形成。 3-（二氯乙酰基）色酮-4 H -1-苯并吡喃-4-酮-杂环胺-稠合吡啶-环化反应
• 2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines
  作者：Viktor O. Iaroshenko、Satenik Mkrtchyan、Ashot Gevorgyan、Mariia Miliutina、Alexander Villinger、Dmytro Volochnyuk、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1039/c1ob06494k

  日期：——

  A divergent and regioselective approach to fused pyridines was developed through formal [3 + 3] cyclocondensations from simple 2,3-unsubstituted chromones or their enaminone precursors.

  通过简单的 2,3-未取代色酮或其烯胺酮前体的正式 [3 + 3] 环缩合反应，开发出了一种不同的、具有区域选择性的方法来制备融合吡啶。
• 3-Methoxalylchromone—a novel versatile reagent for the regioselective purine isostere synthesis
  作者：Satenik Mkrtchyan、Viktor O. Iaroshenko、Sergii Dudkin、Ashot Gevorgyan、Marcelo Vilches-Herrera、Gagik Ghazaryan、Dmitriy M. Volochnyuk、Dmytro Ostrovskyi、Zeeshan Ahmed、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1039/c0ob00379d

  日期：——

  The first synthesis of 3-methoxalylchromone was described. The reaction of the latter with electron-rich aminoheterocycles afforded a set of heteroannelated pyridines bearing a CO2Me substituent located at the α-position of the pyridine core.

  首次描述了 3-甲氧基苯丙酮的合成。后者与富含电子的氨基杂环反应后，得到了一组杂环吡啶，其吡啶核心的δ位上带有 CO2Me 取代基。
• 4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins
  作者：Viktor O. Iaroshenko、Friedrich Erben、Satenik Mkrtchyan、Ani Hakobyan、Marcelo Vilches-Herrera、Sergii Dudkin、Alina Bunescu、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1016/j.tet.2011.08.030

  日期：2011.10

  4-chloro-3-(methoxalyl)coumarins react with electron-rich aminoheterocycles, dimethyl 1,3-acetonedicarboxylate, hydrazines, alkyl thioglycolates, and methyl sarcosinate to give a variety of 3,4-heteroannulated coumarins. The starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride.

  4-氯-3-（三氟乙酰基）-和4-氯-3-（甲氧烷基）香豆素与富含电子的氨基杂环，1,3-丙酮二羧酸二甲酯，肼，烷基硫代乙醇酸酯和肌氨酸甲酯合成各种3， 4异环化香豆素。在三甲基甲硅烷基氯的存在下，通过4-羟基香豆素与三氟乙酸酐和2-氯-2-氧代乙酸甲酯的反应制备起始原料。报道了NMR研究和X射线晶体学分析。
• A general strategy for the synthesis of difluoromethyl-containing pyrazoles, pyridines and pyrimidines
  作者：Viktor O. Iaroshenko、Verena Specowius、Katharina Vlach、Marcelo Vilches-Herrera、Dmytro Ostrovskyi、Satenik Mkrtchyan、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tet.2011.05.085

  日期：2011.8

  Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF2Cl-substituted heterocycles. Subsequent radical reactions with trimethylstannane or allyltrimethylstannane gave difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles, respectively. (C) 2011 Elsevier Ltd. All rights reserved.