Login / Signup

Aryne and CO 2 -based formal [2 + 2 + 2] annulation to access tetrahydroisoquinoline-fused benzoxazinones.

Shiqi LiuKun ZhangYutong MengJiaxi XuNing Chen
Published in: Organic & biomolecular chemistry (2023)
Tetrahydroisoquinoline and its fused polyheterocycles are prevalent structural motifs found in numerous natural products. In this study, we report a highly efficient and convergent synthetic approach for the construction of tetrahydroisoquinoline-fused polyheterocycles through a three-component formal [2 + 2 + 2] annulation process by combining 3,4-dihydroisoquinolines, CO 2 , and benzynes. Notably, electron-rich 3,4-dihydroisoquinolines and electron-deficient benzynes exhibit greater reactivity in this annulation. Moreover, this method benefits from the convergent synthesis and the utilization of carbon dioxide, providing a valuable strategy for the facile synthesis of tetrahydroisoquinoline-fused polyheterocycles, with potential applications in the discovery and development of novel organic molecules.
Keyphrases
  • highly efficient
  • carbon dioxide
  • small molecule
  • high throughput
  • risk assessment
  • solar cells