6-chloro-3-formyl-2-mercaptoquinoline | 887922-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-chloro-3-formyl-2-mercaptoquinoline
• 英文别名: 6-chloro-2-sulfanylidene-1H-quinoline-3-carbaldehyde
• CAS: 887922-70-5
• 化学式: C₁₀H₆ClNOS
• 分子量: 223.683
• InChiKey: AEKBBFWYGCUNND-UHFFFAOYSA-N

物化性质

• 熔点：
  >248 °C(Solv: ethyl acetate (141-78-6); benzene (71-43-2))
• 沸点：
  375.1±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-formyl-2-mercaptoquinoline 在 potassium carbonate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 [(6-氯-3-甲酰基喹啉-2-基)硫代]乙酸乙酯
  参考文献：
  名称：

  Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines

  摘要：

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500601088846
• 作为产物：
  描述：

  2,6-二氯喹啉-3-甲醛 在 盐酸 、 sodium sulfide 作用下， 以 乙醇 为溶剂， 以85%的产率得到6-chloro-3-formyl-2-mercaptoquinoline
  参考文献：
  名称：

  A Fast and Large-Scale Synthesis of 3-Formyl-2-mercaptoquinolines

  摘要：

  A convenient, efficient, and inexpensive procedure for the synthesis of 3-formyl-2-mercaptoquinolines 2a-l has been developed by a simple one-pot reaction of 3-formyl-2-chloroquinolines 1a-l with sodium sulfide and hydrochloric acid in ethanol. The structures of all the synthesized compounds were elucidated on the basis of elemental analyses and IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500600574796

文献信息

• The synthesis of iminothiophenone-fused quinolines and evaluation of their serendipitous reactions
  作者：Morteza Shiri、Zeinab Faghihi、Hossein A. Oskouei、Majid M. Heravi、Shima Fazelzadeh、Behrouz Notash

  DOI：10.1039/c6ra11469e

  日期：——

  The novel synthesis of tricyclic 2-(cyclohexylimino)thieno[2,3-b]quinolin-3(2H)-ones from the reaction of 2-mercaptoquinoline-3-carbaldehydes and isocyanides in methanol without the use of any additive is described. This protocol proceeds with high atom economy through the formation of C–S and C–C bonds and then oxidation via tandem reaction. Moreover, some other remarkable aspects of this reaction

  描述了在不使用任何添加剂的情况下，由2-巯基喹啉-3-甲醛与异氰酸酯在甲醇中反应合成三环2-（环己基氨基）噻吩并[2,3 - b ]喹啉-3（2H）-的新方法。 。该协议通过形成C–S和C–C键，然后通过串联反应进行氧化来实现高原子经济性。此外，还研究了该反应的其他显着方面，例如水解和与芳族胺的三组分反应以产生高度共轭的席夫碱。
• Microwave Induced One-Pot Synthesis of Some New Thiopyrano[2,3-b]quinolin-2-ones under Solvent-Free Conditions
  作者：M. Raghavendra、Halehatty S. Bhojya Naik、Bailure S. Sherigara

  DOI：10.1080/10426500701613170

  日期：2008.4.18

  A series of some new thiopyrano[2,3-b]quinolin-2-one 2a-i have been synthesized by the one pot reaction between 2-mercaptoquinoline-3-carbaldehyde 1a-i and phenoxyacetic acid using TEA catalyst under microwave irradiation in solvent free conditions. The procedure is simple, environmentally benign and occurs in good yields. All the newly synthesized compounds were characterized by elemental analyses

  2-巯基喹啉-3-甲醛1a-i与苯氧乙酸在微波辐照下，以TEA为催化剂，通过一锅反应合成了一系列新型吡喃并[2,3-b]喹啉-2-one 2a-i。无溶剂条件。该程序简单、环境友好且收率良好。所有新合成的化合物均通过元素分析、IR、1H NMR 和质谱数据进行表征。
• Microwave Assisted Synthesis of Some Novel Thiopyrano[2,3-<i>b</i>]quinolines as a New Class of Antimicrobial Agent
  作者：B. P. Nandeshwarappa、D. B. Aruna Kumar、M. N. Kumaraswamy、Y. S. Ravi Kumar、H. S. Bhojya Naik、K. M. Mahadevan

  DOI：10.1080/10426500500366285

  日期：2006.6.1

  A series of novel substituted thiopyrano[2,3-b]quinolines 4a-e, 5a-e, and 6a-e were prepared from substituted 3-formyl-2-mercapto quinolines 2a-e , on reaction with ethyl acetoacetate, diethyl malonate, and ethyl cyanoacetate 3a-c by microwave irradiation in the presence of piperidine. Synthesized compounds were evaluated for antimicrobial activities. Among the compounds tested, 7-chloro-2-oxo-2H-thiopyrano[2,3-b]quinoline-3-carbonitrile 6d and 7-nitro-2-oxo-2H-thiopyrano[2,3-b]quinoline-3-carbonitrile 6e were highly active against S. aureus and M. roseus.
• A Fast and Large-Scale Synthesis of 3-Formyl-2-mercaptoquinolines
  作者：Belalakatte P. Nandeshwarappa、Doyijode B. Aruna Kumar、Halehatty S. Bhojya Naik、Kittappa M. Mahadevan

  DOI：10.1080/10426500600574796

  日期：2006.9.1

  A convenient, efficient, and inexpensive procedure for the synthesis of 3-formyl-2-mercaptoquinolines 2a-l has been developed by a simple one-pot reaction of 3-formyl-2-chloroquinolines 1a-l with sodium sulfide and hydrochloric acid in ethanol. The structures of all the synthesized compounds were elucidated on the basis of elemental analyses and IR, H-1 NMR, and mass spectral data.
• Chemistry of Substituted Quinolines: Thieno[2,3-<b> <i>b</i> </b>] and Thiopyrano[2,3-<b> <i>b</i> </b>]quinolines
  作者：Balaji M. Kiran、Belalakatte P. Nandeshwarappa、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.1080/10426500601088846

  日期：2007.3.15

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.