Late-Stage Functionalization Strategies of 1,2,3-Triazoles: A Post-Click Approach in Organic Synthesis

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

The 1,2,3-triazole scaffolds are an important class of biologically privileged heterocyclic compounds with several key applications in chemistry, biology, medicine, agriculture, and material science. "postclick" functionalization 1,2,3-triazoles may emerge as a promising tactic for the construction molecular architectures therapeutics is considered to be growing area investigation. This interest extends beyond regioselective Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) method that involves trapping Cu(I)-triazole suitable precursors. In this Perspective, we highlight impact postclick strategies organic synthesis required late-stage hope emerging concept provide ample opportunities modern notable medicinal materials

Language: Английский

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Catalytic Enantioselective [4+1]-Annulation of Carboxylic Acids with Cyclopropenes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

An efficient asymmetric synthesis of 3-vinylphthalides has been accomplished through rhodium-catalyzed [4+1]-annulation arylcarboxylic acids with cyclopropenes involving C–H bond functionalization. The method exhibited excellent compatibility for various functional groups and offered diverse substituted in yield enantioselectivity. Synthetic application control experiments were also performed to demonstrate the utility understand reaction pathway.

Language: Английский

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Carbonyl vs Hydroxy: Rhodium catalyzed carbonyl ylide triggered diastereoselective synthesis of 2,5-methano-1,3-benzoxazepines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

A general and efficient rhodium catalyzed chemoselective reaction of N-sulfonyl-1,2,3-triazoles with 2-hydroxyphenyl substituted enone has been successfully accomplished. The occurs through the initial azavinyl carbenes to carbonyl group followed by rearrangement cyclization. tolerated various functional groups allowed synthesis 2,5-methano-1,3-benzoxazepines in high yield as single diastereomer. Control experiments revealed formation potential dihydropyrrole an intermediate aided proposing plausible mechanism.

Language: Английский

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Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7828 - 7833

Published: Sept. 6, 2024

A double dearomatization of dyads consisting 1-sulfonyl-1,2,3-triazoles and 3-aryl-5-methoxyisoxazoles was applied for the efficient synthesis nonfused 1

Language: Английский

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Copper(I)-Catalyzed Tandem Aminobenzannulation of Dienyne with Sulfonyl Azide

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3292 - 3303

Published: Feb. 19, 2024

A general and efficient copper-catalyzed tandem aminobenzannulation of dienyne has been accomplished employing sulfonyl azides as a coupling partner. The reaction involves the formation both C–C C–N bonds via initial generation ketenimine from terminal alkyne azide followed by electrocyclic ring closure aromatization. developed is operationally simple allows synthesis diverse substituted aminonaphthalenes fused aminoarenes in good to excellent yields with high selectivities.

Language: Английский

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Post-functionalization of Click-Derived 1,2,3-Triazoles

Materials horizons, Journal Year: 2024, Volume and Issue: unknown, P. 637 - 670

Published: Jan. 1, 2024

Language: Английский

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Lewis Base Promoted [4+2] Annulation of o-Acylamino-aryl MBH Carbonates with Isatin

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The first example of Lewis base promoted [4 + 2] annulation between

Language: Английский

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Rhodium(II)‐Catalyzed Denitrogenative Transformations of N‐Sulfonyl‐1,2,3‐triazoles

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Abstract N ‐Sulfonyl‐1,2,3‐triazoles are valuable precursors for the generation of α‐imino carbene intermediates in presence metal catalysts, especially rhodium(II) complexes. Due to electrophilic and nucleophilic nitrogen, these reactive can easily be incorporated into many annulations, cycloadditions, C−H or O/N/S−H bond insertions functionalization reactions. A large number pharmaceutically important nitrogen‐based building blocks constructed via this direct atom‐economical strategy. In review, we have described transformations ‐sulfonyl‐1,2,3‐triazoles based on intermediates.

Language: Английский

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Rhodium-Catalyzed One-pot Chemoselective Insertion-Rearrangement-Cyclization of Azavinyl Carbenes with 2-Aminobenzyl Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16351 - 16362

Published: Nov. 4, 2024

Chemoselective insertion of in situ generated α-imino rhodium carbene onto the O–H bond 2-aminobenzyl alcohols over N–H followed by [1,3]-alky shift has been successfully accomplished for synthesis amine tethered ketone derivatives. The resultant product was further cyclized under acidic conditions to afford biologically important 3-aminoquinolines. Successful integration chemoselective insertion-cum-rearrangement and cyclization one pot offered access various 3-aminoquinolines a good yield. Conversion into biological motifs also demonstrated.

Language: Английский

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