NBS-mediated <i>C</i> -selenocyanation/cyclization of enaminones with KSeCN: a mild and efficient synthesis of 2-aminoselenazoles
A simple, exogenous-base-free, and NBS-mediated <i>C</i>-selenocyanation/cyclization reaction of enaminones with KSeCN under mild conditions has been developed, providing a facile synthetic route to 2-aminoselenazole products. This efficient protocol is postulated to proceed <i>via</i> an initial NBS-oxidated polarity reversal of the reactive SeCN<sup>-</sup> anion to form <i>N</i>-selenocyanosuccinimide as an electrophilic selenium source, which can induce the <i>C</i>-selenocyanation of enaminones and enamino esters, followed by a nucleophilic cyclization promoted by the <i>in situ</i> generated HBr.
Authors
- Tianyuan Qin (ORCID: https://orcid.org/0000-0001-9956-3273)
- Yuankang Xin
- Zhuo Chen (ORCID: https://orcid.org/0000-0002-6351-8689)
- Caifeng Yuan
- E Tang (ORCID: https://orcid.org/0000-0003-2382-8479)
- Fei Yuan (ORCID: https://orcid.org/0000-0001-5723-7381)
- Wenxia Hu
- Jianxin Duan
Institutions
- Yunnan University (CN)
- Yunnan Center for Disease Control And Prevention (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00928f
- Primary Topic
- Organoselenium and organotellurium chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Yunnan Provincial Science and Technology Department