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. 2023 Feb 20;13(9):6191-6198.
doi: 10.1039/d2ra07400a. eCollection 2023 Feb 14.

Rhodium-catalyzed selenylation and sulfenylation of quinoxalinones 'on water'

Ram Sunil Kumar Lalji  1   2 , Prince  1 , Mohit Gupta  1   3 , Sandeep Kumar  1 , Amit Kumar  4 , Brajendra Kumar Singh  1
Affiliations

Rhodium-catalyzed selenylation and sulfenylation of quinoxalinones 'on water'

Ram Sunil Kumar Lalji et al. RSC Adv. .

Abstract

A rhodium-catalysed, regioselective synthetic methodology for selenylation and sulfenylation of 3-phenyl quinoxolinones has been developed through N-directed C-H activation in the presence of silver triflimide, and silver carbonate using dichalcogenides 'on water'. The methodology has been proven to be efficient, regioselective and green. Using this method, a range of selenylations and sulfenylations of the substrates has been carried out in good to excellent yields. Further, late-stage functionalisation produced potential anti-tumour, anti-fungal and anti-bacterial agents making these compounds potential drug candidates.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Biologically active organosulphur and organoselenium compounds.
Fig. 2
Fig. 2. Pharmaceutically active quinoxalinones.
Scheme 1
Scheme 1. Substrate scope of 3-phenylquinoxalin-2(1H)-ones and diphenyl diselenides.
Scheme 2
Scheme 2. Substrate scope of 3-phenylquinoxalin-2(1H)-ones and diphenyl(dialkyl) disulfides.
Fig. 3
Fig. 3. Single crystal X-ray structure of the compounds 3a and 3b.
Scheme 3
Scheme 3. Late-stage functionalization of potential anti-tumour and anti-microbial agents.
Scheme 4
Scheme 4. Preliminary mechanistic experiments.
Scheme 5
Scheme 5. H/D exchange and deuterium kinetic isotope studies.
Scheme 6
Scheme 6. Plausible reaction mechanism for the regioselective chalcogenation of phenylquinoxalinones.
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