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DOI: 10.1055/s-0040-1720079
DMSO arbitrated Oxidative Annulation Followed by Homologated N-Alkylation: Microwave-Assisted Efficient and Greener Approach to Access 3-(3-Oxo-3-arylpropyl) Quinazolinones
The authors thank the CSIR - Indian Institute of Chemical Technology (CSIR-IICT). AVG Prasanthi thanks Department of Science and Technology (DST), Ministry of Science and Technology, India for INSPIRE doctoral fellowship.
Abstract
A convenient, time efficient, tandem approach for the synthesis of medicinally privileged 3-(3-oxo-3-arylpropyl) quinazolinones is developed from ubiquitously available acetophenones and anthranilamide via microwave irradiation. This transition-metal-free reaction is initiated by the oxidative annulation of anthranilamide and in situ generation of α,β-unsaturated carbonyl compounds from aryl ketones in the presence of K2S2O8 and dimethyl sulfoxide. The latter acts as a source of two carbons [methine (=CH–) and methylene (–CH2–)] apart from being the solvent. The reaction is carried out under microwave irradiation which has the advantage of homogenous heat distribution, reducing the reaction time drastically compared to the conventional heating reaction.
Keywords
anthranilamide - acetophenones - quinazolinones - oxidative annulation - Michael addition - transition-metal-free synthesis - microwave irradiationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720079.
- Supporting Information
Publication History
Received: 25 May 2023
Accepted after revision: 07 July 2023
Article published online:
08 August 2023
© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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