6-methylmercaptothiocarbonyl-1,3-dimethyl-5-(3-nitrophenyl)-2,4-dioxo-7-(thiophen-2-yl)-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine | 1255769-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 6-methylmercaptothiocarbonyl-1,3-dimethyl-5-(3-nitrophenyl)-2,4-dioxo-7-(thiophen-2-yl)-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine
• 英文别名: Methyl 1,3-dimethyl-5-(3-nitrophenyl)-2,4-dioxo-7-thiophen-2-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carbodithioate
• CAS: 1255769-99-3
• 化学式: C₂₁H₁₈N₄O₄S₃
• 分子量: 486.596
• InChiKey: DHFMWBIFSROFGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  184
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-oxo-3-thiophen-2-yl-dithiopropionic acid methyl ester 、 1,3-二甲基-6-氨基脲嘧啶 、 间硝基苯甲醛 在 H₂SO₄-SiO₂ 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以55%的产率得到6-methylmercaptothiocarbonyl-1,3-dimethyl-5-(3-nitrophenyl)-2,4-dioxo-7-(thiophen-2-yl)-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine
  参考文献：
  名称：

  Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters

  摘要：

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)

  DOI：

  10.1021/jo101572c

文献信息

• Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
  作者：Ganesh Chandra Nandi、Subhasis Samai、Maya Shankar Singh

  DOI：10.1021/jo101572c

  日期：2010.11.19

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)