Activation of enamine by photoexcited organocatalyst assisted singlet oxygen: synthesis of oxazoles and quinoxalines

Elavarasan, Selvaraj; Preety, Jeyaraj; Kesavan, M.; Patel, Ravi B.; Baskar, Baburaj

doi:10.1039/d4ob00609g

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00609g

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Activation of enamine by photoexcited organocatalyst assisted singlet oxygen: synthesis of oxazoles and quinoxalines

Selvaraj Elavarasan,

Jeyaraj Preety,

M. Kesavan

et al.

Abstract: Herein, a novel transition metal-free thiol-based donor-acceptor organo photocatalyst-assisted, singlet oxygen-mediated, tandem oxidative cyclization for the synthesis of substituted oxazoles in moderate to good yields is described. The developed method...

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Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates

Gao,

Wu,

et al. 2024

Molecules

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Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an important pharmacophore, contains both trifluoromethyl and hydroxyl groups and is common in molecules with important biological activities. Constructing oxazoles that contain a trifluoromethyl carbinol unit is undoubtedly important and valuable for expanding the chemical space in drug discovery. In this study, a simple and efficient method was developed for the synthesis of oxazoles containing a CF3-substituted alcohol unit via the tandem cycloisomerization/hydroxyalkylation of N-propargylamides with trifluoropyruvates through a rational Lewis acid catalytic mechanism. This Zn(OTf)2-catalyzed synthetic protocol is operationally simple and provides a series of oxazoles in moderate to good yields. The protocol demonstrates broad substrate scope, high functional group tolerance, and high atom economy and can achieve gram-level reactions, indicating the strong possibility of its practical application.

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Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates

Gao,

Wu,

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

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Activation of enamine by photoexcited organocatalyst assisted singlet oxygen: synthesis of oxazoles and quinoxalines

Abstract: Herein, a novel transition metal-free thiol-based donor-acceptor organo photocatalyst-assisted, singlet oxygen-mediated, tandem oxidative cyclization for the synthesis of substituted oxazoles in moderate to good yields is described. The developed method...

Cited by 1 publication

References 80 publications

Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates

Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates

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