Base- and sulfur-promoted oxidative lactonization of chalcone-acetate Michael adducts: access to pyran-2-ones

Nguyen, Cao Nguyen; Nguyen, Duc Toan; Tran, Ha An; Mac, Dinh Hung; Nguyen, Thi Thu Tram; Retailleau, Pascal; Nguyen, Thanh Binh

doi:10.1039/d4ob00479e

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00479e

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Base- and sulfur-promoted oxidative lactonization of chalcone-acetate Michael adducts: access to pyran-2-ones

Cao Nguyen Nguyen,

Duc Toan Nguyen,

Ha An Tran

et al.

Abstract: A cost-effective, practical, straightforward and scalable synthesis of α-pyrones via base- and sulfur-promoted annulation of phenylacetates and chalcones. Generated in situ from the starting components by using dbu as a...

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Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones

Chen,

Ye,

Huang

et al. 2024

Asian J Org Chem

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An efficient, practical, and scalable Cs2CO3‐catalyzed [4+2] annulation reaction between ynones and acetates is presented, wherein ynones serve as the four‐atom annulation partners. This methodology facilitates the synthesis of substituted 2‐pyrones with yields ranging from good to excellent. The ready availability of the starting materials, coupled with the simplicity of the annulation protocol, renders this approach highly amenable to the preparation of a diverse range of 2‐pyrones. Furthermore, the feasibility of the reaction on a gram scale and its application in the synthesis of a potent and selective cyclooxygenase‐2 inhibitor underscore the practical significance and utility of this method.

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Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones

Chen,

Ye,

Huang

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions

Conen,

Meier

2024

Tetrahedron Chem

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Base- and sulfur-promoted oxidative lactonization of chalcone-acetate Michael adducts: access to pyran-2-ones

Abstract: A cost-effective, practical, straightforward and scalable synthesis of α-pyrones via base- and sulfur-promoted annulation of phenylacetates and chalcones. Generated in situ from the starting components by using dbu as a...

Cited by 2 publications

References 46 publications

Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones

Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones

Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions

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