Synthesis of Benzopyrone-Fused Hydrobenzo[<i>c</i>,<i>d</i>]indoles via Cascade Annulation of <i>p</i>-Quinamines and 3-Formylchromones
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cascade annulation reaction between <i>p</i>-quinamines and 3-formylchromones was developed, affording a series of benzopyrone-fused hydrobenzo[<i>c</i>,<i>d</i>]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.
Authors
- Yun‐Lin Liu (ORCID: https://orcid.org/0000-0001-5902-9885)
- Aiqing Zhong
- Guo‐Shu Chen
- Hai Tao Ren (ORCID: https://orcid.org/0000-0002-8188-1561)
- Cheng Zhao
- Dingxiong Xie
- Chen-Chen Ni
Institutions
- Guiyang Medical University (CN)
- Guangdong University of Foreign Studies (CN)
- Guangzhou University (CN)
- Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences (CN)
- Guangdong Teachers College of Foreign Language and Arts
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-12
- DOI
- https://doi.org/10.1021/acs.orglett.4c02591
- Citations
- 4
- Primary Topic
- Synthesis of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.79
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Guangdong Province
- Bureau of Education of Guangzhou Municipality