Three-Component Reaction toward Polyannulated Quinazolinones, Benzoxazinones, and Benzothiazinones

An efficient conversion of readily accessible cyclic imines with acid chlorides, that are able to take part in nucleophilic aromatic substitution (SNAr) reactions is realized in a new three-component, one-pot reaction, giving at least tricyclic annulated quinazolinones, benzoxazinones, and benzothiazinones as a result of the employed nitrogen, oxygen, or sulfur nucleophiles, respectively. Especially in the case of quinazolinones, this convenient strategy enables the access to heterocycles of heightened diversity, which offer the development of efficient derivatizations of the elaborated heterocyclic scaffolds. In a subsequent Heck or Ullmann cyclization, further annulations to the mentioned quinazolinones can be carried out.本研究开发了一种新型三组分一锅法反应，可高效实现易得环亚胺与可参与亲核芳香取代（nucleophilic aromatic substitution, SNAr）反应的酰氯之间的转化。该反应分别以氮、氧、硫亲核试剂为底物，生成至少三环稠合喹唑啉酮（quinazolinones）、苯并恶嗪酮（benzoxazinones）与苯并噻嗪酮（benzothiazinones）类产物。尤其针对喹唑啉酮类化合物，该便捷策略可制备多样性更为丰富的杂环化合物，为所构建杂环骨架的高效衍生化提供了可行路径。后续可通过Heck反应（Heck）或Ullmann环化反应（Ullmann），对前述喹唑啉酮类化合物进行进一步稠合修饰。