Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and <i>N</i>-Aminopyridinium Salt in Visible Light
We report a visible-light-assisted tandem oxidative 5-<i>exo</i>-dig cyclization of 1,6-enynes for the synthesis of aminated C-3 aryloylated benzofuran, furopyridine, benzothiophene, and indole derivatives. The nitrogen-centered radical generated in situ from <i>N</i>-aminopyridinium salt initiates the consecutive formation of C-N, C-C, and C-O bonds. The methodology exhibits good functional group tolerance and regioselectivity, furnishing products in good to excellent yields at room temperature. Preliminary biological screening of synthesized molecules reveals their potential as anticancer agents.
Authors
- Nidhi Jain (ORCID: https://orcid.org/0000-0001-8645-430X)
- Priya Gupta (ORCID: https://orcid.org/0000-0002-4666-4203)
- Shruti Rajput
- Rajat (ORCID: https://orcid.org/0000-0001-8645-430X)
- Harpal Singh (ORCID: https://orcid.org/0000-0002-8541-4514)
- Nitesh
Institutions
- Indian Institute of Technology Delhi (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.joc.4c02439
- Citations
- 10
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.50
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- Indian Institute of Technology Delhi