3-chloro-4-iodo-1,2,5-thiadiazole | 537706-14-2

• 英文名称: 3-chloro-4-iodo-1,2,5-thiadiazole
• CAS: 537706-14-2
• 化学式: C₂ClIN₂S
• 分子量: 246.459
• InChiKey: NHUVQJGSWZSBEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1,1,1-三丁基甲锡烷)嘧啶 、 3-chloro-4-iodo-1,2,5-thiadiazole 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以76%的产率得到3-氯-4-(吡啶-3-基)-1,2,5-噻二唑
  参考文献：
  名称：

  The Palladium-catalyzed Cross-Coupling Reactions of 3-Chloro-4-halogeno-1,2,5-thiadiazoles

  摘要：

  3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

  DOI：

  10.3987/com-02-9550
• 作为产物：
  描述：

  3-amino-4-chloro-1,2,5-thiadiazole 在 copper(l) iodide 、 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以41%的产率得到3-chloro-4-iodo-1,2,5-thiadiazole
  参考文献：
  名称：

  The Palladium-catalyzed Cross-Coupling Reactions of 3-Chloro-4-halogeno-1,2,5-thiadiazoles

  摘要：

  3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

  DOI：

  10.3987/com-02-9550

文献信息

• Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole
  申请人：Eli Lilly and Company

  公开号：US06620940B1

  公开（公告）日：2003-09-16

  The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

  本发明涉及3-氯-4-卤代-1,2,5-噻二唑化合物，以及生产新型单取代和双取代-1,2,5-噻二唑的方法，还涉及单取代和双取代-1,2,5-噻二唑。