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 CN 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.

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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
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article

Access to 1-aryl-pyrazolin-5-ones via photoinduced chemoselective cyclization of N-methacrylo aldehyde hydrazones

Yangjian Cheng, Changduo Pan, Jin‐Tao Yu, Yu Sheng
13 citations
Chemical Communications
Sulfur-Based Synthesis Techniques
3.25
article

Access to 1-aryl-pyrazolin-5-ones via photoinduced chemoselective cyclization of N-methacrylo aldehyde hydrazones

Yangjian Cheng, Changduo Pan, Jin‐Tao Yu, Yu Sheng
article en
13 citations

Abstract

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 CN 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.

Chemical CommunicationsVol. 61(6)
Jiangsu University of Technology (CN), Changzhou University (CN)
Clean water and sanitation
Openalex Percentile: Top 7%
Sulfur-Based Synthesis Techniques
3.25
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