Domino-Annulation-Based Approach to Synthesize Bridged Bis-thiopyrano[2,3-<i>b</i>]indoles and Unbridged Thiopyrano[2,3-<i>b</i>]indoles
A novel domino strategy for the construction of intricate bridged bis-thiopyrano[2,3-<i>b</i>]indoles was disclosed, which involved one molecule of 3-formylchromones and two molecules of indoline-2-thiones, enabling the formation of four new bonds in a single operation. The transformation occurred under mild reaction conditions, facilitated by the synergistic action of the base NaHCO<sub>3</sub> and the catalytic acid ZnCl<sub>2</sub>. Notably, when these bridged bis-thiopyrano[2,3-<i>b</i>]indole skeletons were treated with alkyl halides under basic conditions, they underwent deconstruction to yield alkylthio-substituted indole-decorated thiopyrano[2,3-<i>b</i>]indoles.
Authors
- Yan-Hui Fu (ORCID: https://orcid.org/0000-0003-1282-2178)
- Kang Zhou (ORCID: https://orcid.org/0009-0008-0925-7079)
- Chun Zhang
- Hongbin Zhai (ORCID: https://orcid.org/0000-0003-2198-1357)
- Taimin Wang (ORCID: https://orcid.org/0000-0001-5730-0555)
- Bin Cheng (ORCID: https://orcid.org/0000-0002-8276-6653)
- Wenjun Zhang (ORCID: https://orcid.org/0000-0002-2677-3752)
- Wei Xu (ORCID: https://orcid.org/0000-0002-6316-5895)
- Wenting Fu (ORCID: https://orcid.org/0009-0002-7134-2182)
Institutions
- Hainan Normal University (CN)
- Shenzhen Polytechnic University (CN)
- Peking University (CN)
- The Polytechnic University of Japan (JP)
- State Key Laboratory of Chemical Engineering (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c00652
- Citations
- 2
- Primary Topic
- Synthesis of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 2.79
Funders
- Department of Education of Guangdong Province
- Science, Technology and Innovation Commission of Shenzhen Municipality
- Basic and Applied Basic Research Foundation of Guangdong Province