Synthesis of Thieno[3,2- <i>b</i> ]thiophene-Cored Hexacyclic Molecules Via the Pictet–Spengler Reaction
]thiophene bisquinoline derivatives via Pictet-Spengler reaction is reported, which were found to be highly versatile. Aromatic aldehydes afforded the desired products in moderate to good yields, with the observed reactivity depending strongly on the substitution pattern. In contrast, aliphatic aldehydes generated desired products only when the α-position of the benzylamine was blocked, while the open α-position yielded non-Pictet-Spengler reaction products, which is ascribed to aldehyde self-condensation or enol-mediated pathways.
Authors
- Yi Lin (ORCID: https://orcid.org/0000-0001-9478-152X)
- Tian Gao (ORCID: https://orcid.org/0000-0002-0460-9919)
- Weihao Da
- Alessandro Troisi (ORCID: https://orcid.org/0000-0002-5447-5648)
- Xia Wu (ORCID: https://orcid.org/0000-0002-2761-9976)
- Jinjing Qiu
- Ruiyao Wang (ORCID: https://orcid.org/0000-0002-2252-6164)
- Chang‐Qi Ma (ORCID: https://orcid.org/0000-0002-9293-5027)
- Xiaochen Liu (ORCID: https://orcid.org/0009-0006-0756-912X)
Institutions
- University of Science and Technology (YE)
- New York Academy of Medicine (US)
- University of Liverpool (GB)
- Chinese Academy of Sciences (CN)
- Suzhou Institute of Nano-tech and Nano-bionics (CN)
- Sichuan University of Science and Engineering (CN)
- Xi’an Jiaotong-Liverpool University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-06-29
- DOI
- https://doi.org/10.1021/acs.orglett.6c02091
- Primary Topic
- Synthesis of heterocyclic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00