Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar DOI

Ramanand Das,

Norein Sakander,

Sanchari Kundu

et al.

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

Published: May 20, 2025

A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.

Language: Английский

Silver-catalyzed direct decarboxylative C H functionalization of azauracils with aliphatic carboxylic acids DOI
Jie Zeng, Hong Zhou, Shenghao Wang

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155619 - 155619

Published: April 1, 2025

Language: Английский

Citations

0
Electron donor–acceptor complex-driven photocatalyst-free synthesis of nitrocyclopropanes DOI Creative Commons
Paula Pérez‐Ramos, Patrícia I. C. Godinho, Raquel G. Soengas

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(19), P. 15155 - 15163

Published: Jan. 1, 2025

Herein, a visible light-promoted metal-free protocol for the synthesis of nitrocyclopropanes is reported, exploiting photochemical activity ternary EDA complex.

Language: Английский

Citations

0
Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2H,4H)-diones via Infrequent 1,2-Hydrogen-Atom Transfer DOI
Mi Wang, Yangyang Wang, Jie Wang

et al.

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

Published: May 19, 2025

1,2,4-Triazine-3,5(2H,4H)-diones are widely present in various drug molecules and bioactive molecules. A visible-light-driven C-H alkylation of 1,2,4-triazine-3,5(2H,4H)-diones via 1,2-hydrogen-atom transfer (1,2-HAT) amide radicals is first reported, providing an environmentally friendly sustainable pathway to enrich the structural functional diversity 1,2,4-triazine-3,5(2H,4H)-diones. This novel protocol characterized by mild metal-free reaction conditions, operationally simple method, good group tolerance. To our delight, other heterocycles, such as isoquinoline coumarin, also undergo reactions construct C(sp2)-C(sp3) bonds infrequent 1,2-HAT under current conditions.

Language: Английский

Citations

0
Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar DOI

Ramanand Das,

Norein Sakander,

Sanchari Kundu

et al.

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

Published: May 20, 2025

A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.

Language: Английский

Citations

0