I<sub>2</sub>-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-<i>b</i>]pyrazolo[3,4-<i>e</i>][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode
In this paper, novel sulfur-containing 1,6-dihydrofuro[3,2-<i>b</i>]pyrazolo[3,4-<i>e</i>][1,4]thiazine skeletons were constructed from the simple and readily available materials enaminone, 5-aminopyrazole, and 1,4-dithiane-2,5-diol. Furthermore, a novel 1,4-dithiane-2,5-diol reaction mode has been developed through a double-dipole-reversal process induced by iodine that results in the formation of six new bonds and two new rings in a one-pot reaction. This method shows good substrate compatibility, and the products can be further modified with a variety of pharmaceuticals. Additionally, this novel skeleton exhibits good fluorescence properties in solution, enabling bright and stable green fluorescence imaging in HeLa cells.
Authors
- You Zhou (ORCID: https://orcid.org/0009-0007-5054-1875)
- An‐Xin Wu (ORCID: https://orcid.org/0000-0001-7673-210X)
- Xiang‐Long Chen (ORCID: https://orcid.org/0009-0005-0754-5809)
- Yan‐Dong Wu (ORCID: https://orcid.org/0000-0003-0589-7155)
- Li‐Sheng Wang (ORCID: https://orcid.org/0009-0007-3001-6889)
- Kai‐Lu Zheng
- Xi Shen (ORCID: https://orcid.org/0009-0000-0506-0561)
- Zhi‐Cheng Yu
Institutions
- Guangdong Medical College (CN)
- Guangdong Pharmaceutical University (CN)
- Central China Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-06
- DOI
- https://doi.org/10.1021/acs.orglett.4c02813
- Citations
- 4
- Primary Topic
- Phenothiazines and Benzothiazines Synthesis and Activities
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Higher Education Discipline Innovation Project
- Basic and Applied Basic Research Foundation of Guangdong Province