N-methylmorpholinium 3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate | 1391631-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-methylmorpholinium 3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate
• CAS: 1391631-80-3
• 化学式: C₅H₁₁NO*C₁₄H₁₄N₂O₂S
• 分子量: 375.492
• InChiKey: OIVDSXZSWNQXHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.59
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-methylmorpholinium 3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate 、 ethyl 6-(bromomethyl)-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 以 乙醇 为溶剂， 以51%的产率得到ethyl 6-{[3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetra-hydropyridin-2-ylthio]methyl}-4-(4-meth-oxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

  摘要：

  Alkylation of N-methylmorpholinium 4-Ar-1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar-1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar-1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

  DOI：

  10.1007/s10593-012-1016-0
• 作为产物：
  描述：

  N-甲基吗啉 以 乙醇 为溶剂， 反应 1.0h， 生成 N-methylmorpholinium 3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate
  参考文献：
  名称：

  Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

  摘要：

  Alkylation of N-methylmorpholinium 4-Ar-1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar-1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar-1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

  DOI：

  10.1007/s10593-012-1016-0

文献信息

• Synthesis of thiazolo[3,2-<i>a</i>]pyridines via an unusual Mannich-type cyclization
  作者：Victor V. Dotsenko、Ivan S. Bushmarinov、Alexander S. Goloveshkin、Elena A. Chigorina、Konstantin A. Frolov、Sergey G. Krivokolysko

  DOI：10.1080/10426507.2016.1224877

  日期：2017.1.2

  with 3-(1,3-benzodioxol-5-yl)-2-methylpropanal (ocean propanal) and p-toluidine afforded 7-aryl-2-(1,3-benzodioxol-5-ylmethyl)-2-methyl-3-[(4-methylphenyl)amino]-5-oxo-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyridine-8-carbonitriles in modest (25–46%) yields. The structure of the key compound was confirmed by X-ray crystal structure analysis. GRAPHICAL ABSTRACT

  摘要 N-甲基吗啉鎓 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates 与 3-(1,3-benzodioxol-5-yl)- 2-甲基丙醛（海洋丙醛）和对甲苯胺得到 7-芳基-2-（1,3-苯并二恶醇-5-基甲基）-2-甲基-3-[（4-甲基苯基）氨基]-5-氧代-2 ,3,6,7-四氢-5H-噻唑并[3,2-a]吡啶-8-腈的产率适中（25-46%）。通过X射线晶体结构分析确认了关键化合物的结构。图形概要
• Design and Synthesis of Pyrido[2,1-<i>b</i>][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction
  作者：Victor V. Dotsenko、Konstantin A. Frolov、Tatyana M. Pekhtereva、Olena S. Papaianina、Sergey Yu. Suykov、Sergey G. Krivokolysko

  DOI：10.1021/co5000807

  日期：2014.10.13

  This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.
• Mannich reaction in the synthesis of N,S-containing heterocycles. 14*. Unexpected formation of thiazolo[3,2-a]pyridines in the aminoalkylation of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates by isobutyraldehyde and primary amines
  作者：V. V. Dotsenko、S. G. Krivokolysko

  DOI：10.1007/s10593-012-1042-y

  日期：2012.7

  Treatment of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with an excess of isobutyraldehyde and primary aromatic amines in refluxing ethanol gives the corresponding 7-aryl-3-arylamino-2,2-dimethyl-5-oxo-2,3,6,7-tetrahydro-5 H-thiazolo[3,2-a]pyridine-8-carbonitriles in 18-38 % yields.