Lewis acid-mediated transformations of 5-acyl-<i>N</i>-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles

Janecký, Lukáš; Beier, Petr

doi:10.1039/d4ra01707b

RSC Adv.

2024

DOI: 10.1039/d4ra01707b

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Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles

Lukáš Janecký,

Petr Beier

Abstract: 2-N-Substituted indenones, cyclopentenones or 4-carbonyl oxazoles are prepared from 5-acylated N-fluoroalkyl substituted 1,2,3-triazoles and Lewis acids.

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Cited by 2 publications

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Access to Bicyclo[3.1.0]hexane and Cyclopenta[c]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles

Barashkova,

Gevondian,

Latyshev

et al. 2024

Org. Lett.

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Divergent access to bicyclo[3.1.0]hexane and cyclopenta[c]pyrazole scaffolds bearing azole and azine units has been developed. The approach involves intramolecular cyclization of 5-iodo-1,2,3-triazoles acting as stable diazoimine precursors with concomitant noncatalytic (3 + 2)-cycloaddition. The choice of solvent allows control of the outcome of the cascade transformation. The developed procedure is simple and cost-efficient and allowed important heterocycles to be obtained in one-pot with various functional groups.

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Access to Bicyclo[3.1.0]hexane and Cyclopenta[c]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles

Barashkova,

Gevondian,

Latyshev

et al. 2024

Org. Lett.

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Transformation of 5-acylated N-fluoroalkyl-1,2,3-triazoles to trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and 1,3-oxazin-6-ones via ketenimines

Janecký,

Klepetářová,

Beier

2024

RSC Adv.

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Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles

Abstract: 2-N-Substituted indenones, cyclopentenones or 4-carbonyl oxazoles are prepared from 5-acylated N-fluoroalkyl substituted 1,2,3-triazoles and Lewis acids.

Cited by 2 publications

References 33 publications

Access to Bicyclo[3.1.0]hexane and Cyclopenta[c]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles

Access to Bicyclo[3.1.0]hexane and Cyclopenta[c]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles

Transformation of 5-acylated N-fluoroalkyl-1,2,3-triazoles to trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and 1,3-oxazin-6-ones via ketenimines

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