Access to 1-aryl-pyrazolin-5-ones <i>via</i> photoinduced chemoselective cyclization of <i>N</i>-methacrylo aldehyde hydrazones
A photocatalytic sulfamoylation/5-<i>endo-trig</i> cyclization of (<i>E</i>)-<i>N</i>'-arylidene-<i>N</i>-phenylmethacrylohydrazides with sulfamoyl chlorides was developed. The chemoselective intramolecular addition of the carbon-centered radical intermediate to the CN bond in the hydrazone motif gave the sulfamoylated pyrazolin-5-one. Besides, sulfonyl chlorides are also suitable reaction partners to access sulfonylated pyrazolin-5-ones. This approach is characterized by mild reaction conditions, broad substrates scope, excellent selectivity and the late-stage modification of drug molecules.
Authors
- Yangjian Cheng (ORCID: https://orcid.org/0000-0001-9688-0126)
- Changduo Pan (ORCID: https://orcid.org/0000-0001-5878-3835)
- Jin‐Tao Yu (ORCID: https://orcid.org/0000-0002-0264-9407)
- Yu Sheng (ORCID: https://orcid.org/0000-0002-8210-4334)
Institutions
- Jiangsu University of Technology (CN)
- Changzhou University (CN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2024-12-13
- DOI
- https://doi.org/10.1039/d4cc05976j
- Citations
- 13
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 3.25