N-allyl-2-chloro-4-(2-furyl)pyridin-3-amine | 1359769-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-allyl-2-chloro-4-(2-furyl)pyridin-3-amine
• CAS: 1359769-05-3
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: OHHSFXRCOUEKMW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-allyl-2-chloro-4-(2-furyl)pyridin-3-amine 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 7.0h， 以92%的产率得到4-chlorobenzo[c][1,7]naphthyridine
  参考文献：
  名称：

  Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

  摘要：

  A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.

  DOI：

  10.1021/jo3027033

文献信息

• Synthesis of complex fused polycyclic heterocycles utilizing IMDAF reactions of allylamino- or allyloxy-furyl(hetero)arenes
  作者：Matthew L. Read、Andreas Krapp、Pedro O. Miranda、Lise-Lotte Gundersen

  DOI：10.1016/j.tet.2011.12.079

  日期：2012.2

  carrying a halogen and an amino- or hydroxy group have been converted to allylamino- or allyloxy-furyl-(hetero)arenes. These compounds underwent IMDAF reactions to give complex fused polycyclic heterocycles. The reactivity of the substrates was highly dependent on the detailed substitution pattern, however cyclizations occurred with high stereoselectivity in most cases. Experimental findings regarding

  带有卤素和氨基或羟基的芳烃和杂芳烃已被转化为烯丙基氨基-或烯丙氧基-呋喃基-（杂）芳烃。这些化合物进行IMDAF反应，得到复杂的稠合多环杂环。底物的反应性高度依赖于详细的取代模式，但是在大多数情况下，环化反应以高立体选择性发生。计算支持了有关反应性和立体选择性的实验发现。