DMSO as a dual carbon synthon in one-pot tandem synthesis of -alkylated quinazolinones from anthranilamides and acetophenones

A new, efficient, metal-free, and DMSO-assisted approach for the synthesis of N -alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones in the presence of an oxidizing agent has been developed. In this unique tandem reaction, DMSO played a dual role, acting as a sol...

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Veröffentlicht in:New journal of chemistry 2022-08, Vol.46 (34), p.16289-16296
Hauptverfasser: Yadav, Pushpendra, Yadav, Sourabh, Awasthi, Annapurna, Phanindrudu, Mandalparthi, Bhowmick, Suman, Tiwari, Dharmendra Kumar
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Zusammenfassung:A new, efficient, metal-free, and DMSO-assisted approach for the synthesis of N -alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones in the presence of an oxidizing agent has been developed. In this unique tandem reaction, DMSO played a dual role, acting as a solvent as well as a dual carbon synthon, making this process an environmentally benign approach to accessing medicinally prevalent N -alkylated quinazolinones. The DMSO-assisted in situ generation of an iminium cation and α,-unsaturated ketones from 2-aminobenzamide and aryl methyl ketones, respectively, is the key feature involved in this method. DMSO-assisted approach for the synthesis of N -alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones has been developed. DMSO played a dual role, acting as a solvent as well as a dual carbon synthon, making this process an environmentally benign approach.
ISSN:1144-0546
1369-9261
DOI:10.1039/d2nj01428a