DMSO arbitrated Oxidative Annulation Followed by Homologated N-Alkylation: Microwave-Assisted Efficient and Greener Approach to Access 3-(3-Oxo-3-arylpropyl) Quinazolinones

A. V. G. Prasanthi; Bathini Nagendra Babu

doi:10.1055/s-0040-1720079

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2023; 07(03): 313-321
DOI: 10.1055/s-0040-1720079

paper

DMSO arbitrated Oxidative Annulation Followed by Homologated N-Alkylation: Microwave-Assisted Efficient and Greener Approach to Access 3-(3-Oxo-3-arylpropyl) Quinazolinones

A. V. G. Prasanthi

^aFluoro & Agrochemicals, CSIR - Indian Institute of Chemical Technology, Hyderabad - 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad - 201002, India

,

Bathini Nagendra Babu ∗

^aFluoro & Agrochemicals, CSIR - Indian Institute of Chemical Technology, Hyderabad - 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad - 201002, India

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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 irradiation

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