7-Amino-2-(4-chloro-phenyl)-5-methylsulfanyl-4-nitro-pyrazolo[1,5-a]pyridine-6-carbonitrile | 174749-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-Amino-2-(4-chloro-phenyl)-5-methylsulfanyl-4-nitro-pyrazolo[1,5-a]pyridine-6-carbonitrile
• 英文别名: 7-Amino-2-(4-chlorophenyl)-5-methylsulfanyl-4-nitropyrazolo[1,5-a]pyridine-6-carbonitrile
• CAS: 174749-94-1
• 化学式: C₁₅H₁₀ClN₅O₂S
• 分子量: 359.796
• InChiKey: DLOURJBTUVQJOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-Amino-2-(4-chloro-phenyl)-5-methylsulfanyl-4-nitro-pyrazolo[1,5-a]pyridine-6-carbonitrile 、 丁炔二酸二乙酯 在 potassium phosphate 作用下， 以 二甲基亚砜 为溶剂， 以56%的产率得到9-(4-Chloro-phenyl)-7-nitro-4H-1,4,10,10a-tetraaza-cyclopenta[a]phenalene-2,3,5,6-tetracarboxylic acid tetraethyl ester
  参考文献：
  名称：

  Synthesis of Polycyclic Nitrogen-containing Heterocycles: One Pot Formation of 1,6-Naphthyridine Ring System by Reaction of Amino-cycano-methylyhio-heterocycles with Dialkyl Acetylenedicarboxylates

  摘要：

  The reaction of 5-amino-6-cyano-1,3-dimethyl-7-methylthiopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (1c) with dimethyl acetylenedicarboxylate (DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave tetramethyl 8,9,10,11-tetrahydro-8,10-dimethyl-9,10-dioxo-4H-pyrimido[4',5':5,6]pyrido[2,3,4-cb][1,6]naphthyridine-2,3,5,6-tetracarboxylate (2c). The reaction of other heterocycles bearing amino, cyano, and methylthio groups with DMAD or DEAD under the same reaction conditions gave the corresponding tetracyclic heterocycles containing the fundamental 1,6-naphthyridine ring system.

  DOI：

  10.3987/com-95-s13
• 作为产物：
  描述：

  [双(甲硫基)亚甲基]丙烷二腈 、 3-(4-Chloro-phenyl)-5-nitromethyl-1H-pyrazole 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以91%的产率得到7-Amino-2-(4-chloro-phenyl)-5-methylsulfanyl-4-nitro-pyrazolo[1,5-a]pyridine-6-carbonitrile
  参考文献：
  名称：

  多环含氮杂环†的合成：通过氨基-氰基-甲硫基杂环与乙酰基二羧酸二烷基酯的反应，一锅法形成1,6-萘啶环系统

  摘要：

  在碳酸钾存在下，使3-氨基-3-甲硫基-2-氰基丙烯腈（1）与过量的乙炔基二羧酸二甲酯（DMAD）反应，生成新的三环杂环，六甲基l H -1,4,7-三氮杂萘-2,3,5,6,8,9-六羧酸盐（5a）。当在该反应中使用一当量的DMAD时，获得4-氨基-3-氰基-2-甲基硫代吡啶二甲基-5,6-二羧酸二甲酯（3a），其为5a的关键中间体。

  DOI：

  10.1002/jhet.5570380518

文献信息

• Synthesis of polycyclic nitrogen-containing heterocyclic: One pot formation of 1,6-naphthyridine ring system by reaction of amino-cyano-methylthio-heterocycles with dialkyl acetyeledicarboxylates
  作者：Yoshinori Tominaga、Kenichi Nomoto、Noriko Yoshioka

  DOI：10.1002/jhet.5570380518

  日期：2001.9

  Reaction of 3-amino-3-methylthio-2-cyanoacrylonitrile (1) with excess dimethyl acetylenedi-carboxylate(DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave a novel tricyclic heterocycle, hexamethyl lH-1,4,7-triazaphenalene-2,3,5,6,8,9-hexacarboxylate (5a). When one equivalent of DMAD was used in this reaction, dimethyl 4-amino-3-cyano-2-methylthiopyridine-5,6-dicarboxylate (3a),

  在碳酸钾存在下，使3-氨基-3-甲硫基-2-氰基丙烯腈（1）与过量的乙炔基二羧酸二甲酯（DMAD）反应，生成新的三环杂环，六甲基l H -1,4,7-三氮杂萘-2,3,5,6,8,9-六羧酸盐（5a）。当在该反应中使用一当量的DMAD时，获得4-氨基-3-氰基-2-甲基硫代吡啶二甲基-5,6-二羧酸二甲酯（3a），其为5a的关键中间体。
• Synthesis of Polycyclic Nitrogen-containing Heterocycles: One Pot Formation of 1,6-Naphthyridine Ring System by Reaction of Amino-cycano-methylyhio-heterocycles with Dialkyl Acetylenedicarboxylates
  作者：Yoshinori Tominaga、Noriko Yoshioka

  DOI：10.3987/com-95-s13

  日期：——

  The reaction of 5-amino-6-cyano-1,3-dimethyl-7-methylthiopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (1c) with dimethyl acetylenedicarboxylate (DMAD) in the presence of potassium carbonate in dimethyl sulfoxide gave tetramethyl 8,9,10,11-tetrahydro-8,10-dimethyl-9,10-dioxo-4H-pyrimido[4',5':5,6]pyrido[2,3,4-cb][1,6]naphthyridine-2,3,5,6-tetracarboxylate (2c). The reaction of other heterocycles bearing amino, cyano, and methylthio groups with DMAD or DEAD under the same reaction conditions gave the corresponding tetracyclic heterocycles containing the fundamental 1,6-naphthyridine ring system.