(3-isothiocyanatopyridin-4-yl)phenylmethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-isothiocyanatopyridin-4-yl)phenylmethanone
• 英文别名: (3-Isothiocyanatopyridin-4-yl)-phenylmethanone；(3-isothiocyanatopyridin-4-yl)-phenylmethanone
• 化学式: C₁₃H₈N₂OS
• 分子量: 240.285
• InChiKey: HBFDAKJWJFYDLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-isothiocyanatopyridin-4-yl)phenylmethanone 、 2-溴乙胺氢溴酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以88%的产率得到5-phenyl-2,3-dihydro-5H-pyrido[3,4-d]thiazolo[3,2-a]pyrimidin-5-ol
  参考文献：
  名称：

  A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines

  摘要：

  The reaction of aryl(3-isothiocyanatopyridin-4-yl)methanones, prepared easily from commercially available 3-aminopyridine, with primary amines at room temperature afforded 3-substituted 4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones in good yields. These ketones could be converted to new tricyclic heterocyclic systems, 2,3-dihydro-5H-pyrido[3,4-d]thiazolo [3,2-a]pyrimidine and 3,4-dihydro-2H,6H-pyrido [3',4':4,5]-pyrimido[2,1-b] [1,3]thiazine, upon treatment with 2-bromoethanamine hydrobromide and 3-bromopropaneamine hydrobromide, respectively, in the presence two equivalents of triethylamine.

  DOI：

  10.3987/com-14-13058
• 作为产物：
  描述：

  (3-isocyanopyridin-4-yl)(phenyl)methanone 在 selenium 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(3-isothiocyanatopyridin-4-yl)phenylmethanone
  参考文献：
  名称：

  A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines

  摘要：

  The reaction of aryl(3-isothiocyanatopyridin-4-yl)methanones, prepared easily from commercially available 3-aminopyridine, with primary amines at room temperature afforded 3-substituted 4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones in good yields. These ketones could be converted to new tricyclic heterocyclic systems, 2,3-dihydro-5H-pyrido[3,4-d]thiazolo [3,2-a]pyrimidine and 3,4-dihydro-2H,6H-pyrido [3',4':4,5]-pyrimido[2,1-b] [1,3]thiazine, upon treatment with 2-bromoethanamine hydrobromide and 3-bromopropaneamine hydrobromide, respectively, in the presence two equivalents of triethylamine.

  DOI：

  10.3987/com-14-13058

文献信息

• A Simple Synthesis of 4-Hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thione Derivatives by the Reaction of 3-Isothiocyanatopyridin-4-yl Ketones with Primary Amines
  作者：Kazuhiro Kobayashi、Hiroki Inouchi、Manami Konishi

  DOI：10.3987/com-14-13058

  日期：——

  The reaction of aryl(3-isothiocyanatopyridin-4-yl)methanones, prepared easily from commercially available 3-aminopyridine, with primary amines at room temperature afforded 3-substituted 4-aryl-4-hydroxy-3,4-dihydropyrido[3,4-d]pyrimidine-2(1H)-thiones in good yields. These ketones could be converted to new tricyclic heterocyclic systems, 2,3-dihydro-5H-pyrido[3,4-d]thiazolo [3,2-a]pyrimidine and 3,4-dihydro-2H,6H-pyrido [3',4':4,5]-pyrimido[2,1-b] [1,3]thiazine, upon treatment with 2-bromoethanamine hydrobromide and 3-bromopropaneamine hydrobromide, respectively, in the presence two equivalents of triethylamine.