Direct Access to Strained Fused Dihalo-Aziridino Quinoxalinones via C3-Alkylation Followed by Tandem Cyclization

Quinoxalinones are a privileged class of compounds, and their structural framework is found in many bioactive compounds, natural compounds, and pharmaceuticals. Quinoxalinone is a promising scaffold for different types of functionalization, and the slight modification of the quinoxalinone skeleton i...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-07, Vol.88 (13), p.8010-8023
Main Authors: Khade, Vikas V., Bhowmick, Anindita, Thube, Archana S., Bhat, Ramakrishna G.
Format: Article
Language:English
Subjects:
Alkylation
Cyclization
Drug Discovery
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Summary:Quinoxalinones are a privileged class of compounds, and their structural framework is found in many bioactive compounds, natural compounds, and pharmaceuticals. Quinoxalinone is a promising scaffold for different types of functionalization, and the slight modification of the quinoxalinone skeleton is known to offer a wide range of compounds for drug discovery. Owing to the importance of the quinoxalinone scaffold, we have developed a base-mediated protocol for the C3-alkylation of quinoxalinone followed by tandem cyclization to access novel types of strenuous and fused dihalo-aziridino-quinoxalinone heterocycles via the construction of C–C and C–N bonds. The protocol proved to be simple and practical to access desired fused quinoxalinone heterocycles in excellent yields (up to 98% yield). As an application, the highly functionalized fused dihalo-aziridino-quinoxalinone molecule has been further utilized for mono-dehalogenation under visible light irradiation and selective amide reduction. Moreover, the protocol has also been demonstrated on a gram scale.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00033