I<sub>2</sub>-Promoted Chemoselective Annulative Coupling of 2-Aminobenzamides with Sulfoxonium Ylides: Easy Access to Quinazolinones

A flexible and metal-free synthetic approach for synthesizing 2-benzoyl quinazolinones and 2-aryl quinazolinones via molecular iodine-mediated annulative coupling of sulfoxonium ylides with 2-aminobenzamides has been disclosed. The method demonstrates remarkable chemoselectivity and efficiency, leading to high yields of 2-benzoyl quinazolinones and 2-aryl quinazolinones under optimized conditions. The broad substrate scope, scalability, and practical utility were highlighted through diverse applications, including gram-scale reactions and the synthesis of biologically significant compounds such as tryptanthrin and the chemo/biosensor derivative.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-20
DOI
https://doi.org/10.1021/acs.joc.4c01354
Citations
9
Primary Topic
Quinazolinone synthesis and applications
Type
article
Field-Weighted Citation Impact
2.25

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article

I2-Promoted Chemoselective Annulative Coupling of 2-Aminobenzamides with Sulfoxonium Ylides: Easy Access to Quinazolinones

Ajay Kant Gola, Satyendra Kumar Pandey, Naveen Kumar
9 citations
The Journal of Organic Chemistry
Quinazolinone synthesis and applications
2.25
article

I2-Promoted Chemoselective Annulative Coupling of 2-Aminobenzamides with Sulfoxonium Ylides: Easy Access to Quinazolinones

Ajay Kant Gola, Satyendra Kumar Pandey, Naveen Kumar
article en
9 citations

Abstract

A flexible and metal-free synthetic approach for synthesizing 2-benzoyl quinazolinones and 2-aryl quinazolinones via molecular iodine-mediated annulative coupling of sulfoxonium ylides with 2-aminobenzamides has been disclosed. The method demonstrates remarkable chemoselectivity and efficiency, leading to high yields of 2-benzoyl quinazolinones and 2-aryl quinazolinones under optimized conditions. The broad substrate scope, scalability, and practical utility were highlighted through diverse applications, including gram-scale reactions and the synthesis of biologically significant compounds such as tryptanthrin and the chemo/biosensor derivative.

The Journal of Organic ChemistryVol. 89(17)
Banaras Hindu University (IN)
Science and Engineering Research Board
Openalex Percentile: Top 12%
Quinazolinone synthesis and applications
2.25
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