Iodine-Mediated Oxidative Cyclization of Amino-heteroaromatics with Allylic Alcohols and Propene Derivatives: Access to Pyrazolo[3,4-<i>b</i>]pyridines
An I<sub>2</sub>/BF<sub>3</sub>·Et<sub>2</sub>O-mediated oxidative annulation of allylic alcohols/propene derivatives with 5-aminopyrazoles to construct pyrazolo[3,4-<i>b</i>]pyridines was developed. I<sub>2</sub> mediates both allylic alcohol oxidation and 5-aminopyrazole iodination, enabling a BF<sub>3</sub>·Et<sub>2</sub>O-promoted radical addition/cyclization cascade, while propene derivatives instead proceed via 2-methylallyl iodide intermediates. This allylic alcohol-based methodology not only establishes allylic alcohols as efficient carbon synthons for pyrazolo[3,4-<i>b</i>]pyridine construction but also demonstrates successful gram-scale applicability.
Authors
- Chunping Dong (ORCID: https://orcid.org/0000-0002-3120-5901)
- Qingfu Zhang (ORCID: https://orcid.org/0000-0002-5788-7023)
- Xiaojiao Du (ORCID: https://orcid.org/0000-0002-5633-6481)
- W. Qin (ORCID: https://orcid.org/0000-0001-7703-3132)
- Mei Xin (ORCID: https://orcid.org/0000-0002-3244-9844)
- Jian Li (ORCID: https://orcid.org/0000-0001-6713-1302)
- Caijuan Hu
Institutions
- Kunming University of Science and Technology (CN)
- Changzhou Institute of Technology (CN)
- Precision for Medicine (United States) (US)
- Changzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-16
- DOI
- https://doi.org/10.1021/acs.orglett.5c02151
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China