N-methylmorpholinium 4-(2-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methylmorpholinium 4-(2-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate
• 英文别名: 4-(2-chlorophenyl)-5-cyano-6-sulfanyl-3,4-dihydropyridin-2-olate;4-methylmorpholin-4-ium
• 化学式: C₅H₁₁NO*C₁₂H₉ClN₂OS
• 分子量: 365.884
• InChiKey: SCJOLEXLRQJDQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-methylmorpholinium 4-(2-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

  摘要：

  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.

  DOI：

  10.1021/co5000807
• 作为产物：
  描述：

  3-(o-chlorophenyl)-2-cyanothioacrylamide 以 乙醇 为溶剂， 生成 N-methylmorpholinium 4-(2-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate
  参考文献：
  名称：

  Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

  摘要：

  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.

  DOI：

  10.1021/co5000807

文献信息

• Synthesis of derivatives of a novel heterocyclic system 7-thia-1,4,6,8-tetraazabenzo[de]anthracene
  作者：Victor V. Dotsenko、Elena A. Chigorina、Sergey G. Krivokolysko

  DOI：10.1007/s10593-017-2103-z

  日期：2017.5

  8,9,10,11-tetrahydro-7-thia-1,4,6,8-tetraazabenzo[de]anthracene, were obtained by interaction of 5Н-pyrido[2′,3′:2,3]thiopyrano[4,5-b]pyridines, formed by treating N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with malononitrile dimer, Ас2О or carboxylic acid chlorides.

  新型杂环体系的衍生物8,9,10,11-四氢-7-thia-1,4,6,8-四氮杂苯并[ de ]蒽，是通过5Н-吡啶基[2'，3'的相互作用而获得的：2,3]硫代吡喃并[4,5- b ]吡啶，是通过丙二腈二聚体处理N-甲基吗啉鎓4-芳基-3-氰基-6-氧代-1,4,5,6-四氢吡啶-2-硫醇盐而形成的， Ас 2 О或羧酸氯化物。
• 2-Amino-9-aryl-3-cyano-4-methyl-7-oxo-6,7,8,9-tetrahydropyrido[2′,3′:4,5]thieno[2,3-b]pyridine derivatives as selective progesterone receptor agonists
  作者：Yonghui Wang、Chaya Duraiswami、Kevin P. Madauss、Thuy B. Tran、Shawn P. Williams、Su-Jun Deng、Todd L. Graybill、Marlys Hammond、David G. Jones、Eugene T. Grygielko、Jeffrey D. Bray、Scott K. Thompson

  DOI：10.1016/j.bmcl.2009.07.100

  日期：2009.9

  High throughput screening of the corporate compound collection led to the identification of a novel series of 2-amino-9-aryl-3-cyano-4-methyl-7-oxo-6,7,8,9-tetrahydropyrido[2',3':4,5]thieno[2,3-b]pyridine derivatives as selective PR agonists. Initial SAR exploration leading to potent and selective agonists 9 and 11, X-ray crystal structure of 9 bound to PR-LBD and preliminary developability data are described. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, properties, and structures of ammonium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates
  作者：V. N. Nesterov、S. G. Krivokolysko、V. V. Dotsenko、V. P. Litvinov

  DOI：10.1007/bf02496132

  日期：1997.5

  The reaction of arylcyanomethylenethioacetamides with Meldrum acid gave Michael adducts as ammonium salts. When heated in alcohol, these salts undergo cyclization to ammonium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates. The structure of N-methylmorpholinium 4-(2'-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate was established by X-ray structural analysis.
• ——
  作者：V. V. Dotsenko、S. G. Krivokolysko、V. P. Litvinov

  DOI：10.1023/a:1023033027915

  日期：——
• ——
  作者：V. V. Dotsenko、S. G. Krivokolysko、A. N. Chernega、V. P. Litvinov

  DOI：10.1023/a:1024420930528

  日期：——

  The reactions of N-methylmorpholinium 4-aryl(hetaryl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates with malononitrile and acetone in ethanol afforded substituted tetrahydropyridothienopyridinones. In the absence of acetone, tetrahydropyridothiopyranopyridinones were isolated as the major reaction products. The latter were also synthesized independently by the reactions of the above-mentioned thiolates with 2-amino-1,1,3-tricyanopropene. The structure of 2,4-diamino-10-(2-chlorophenyl)-3-cyano-5-imino-8-oxo-7,8,9,10-tetrahydro-5H-pyrido[2',3':2,3]thiopyrano[4,5-b]pyridine was established by X-ray diffraction analysis.