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Synthesis of Benzopyrone-Fused Hydrobenzo[ c , d ]indoles via Cascade Annulation of p -Quinamines and 3-Formylchromones.

Cheng ZhaoAi-Qing ZhongDing-Xiong XieHai RenChen-Chen NiGuo-Shu ChenYun-Lin Liu
Published in: Organic letters (2024)
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cascade annulation reaction between p -quinamines and 3-formylchromones was developed, affording a series of benzopyrone-fused hydrobenzo[ c , d ]indoles in moderate to high yields with excellent diastereoselectivity. This cascade reaction is efficient since two new rings as well as one C-N, one C═C, and two C-C bonds are created in a single step. The scale-up synthesis and versatile transformations of the products further demonstrated the practicality and utility of this approach.
Keyphrases
  • high intensity
  • room temperature
  • electron transfer