Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(7)

Published: Jan. 19, 2024

Abstract A Minisci‐type carbamoylation of azauracils was developed to afford 6‐carbamoyl in yields up 94 %. In this transformation, oxamic acids were employed as the carbamoyl radical sources under metal‐free conditions. It features high atom economy, good functional group compatibility and convenient operation.

Language: Английский

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Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride

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

Published: March 31, 2025

In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one most explored molecules for study and gained significant attention in organic chemistry due their versatile reactivity, particularly Michael addition reactions. study, trifluoromethanesulfonic anhydride (Tf2O) was used as an activating agent p-QMs, aiming achieve 1,6-Michael products least reported 1,8-Michael with pyridine substituents. The reactivity p-QMs derived from demonstrated distinct reaction pathways, leading formation δ γ lactones. investigation also involved synthesizing a 1-indanone carboxylic acids obtained 1,6-addition.

Language: Английский

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DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2003 - 2007

Published: March 12, 2024

Abstract A DBU‐promoted [3+2] cyclization/retro‐Mannich cascade reaction of N ‐aminoisoquinolinium and ‐aminoquinolinium derivatives with para ‐quinone methides has been established, employing a C=C double bond cleavage. broad range salts, are well tolerated, providing the corresponding rearrangement products. Moreover, scaled‐up reactions diverse derivatizations products were also investigated discussed.

Language: Английский

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1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-promoted regiospecific 1,6-hydroarylation of para-quinone methides with N-heteroarenes: Synthesis of unsymmetrical triarylmethanes

Tetrahedron, Journal Year: 2024, Volume and Issue: 158, P. 133982 - 133982

Published: April 7, 2024

Language: Английский

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Cascade Cyclizations Triggered by Photochemically Generated Carbamoyl Radicals Derived from Alkyl Amines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11801 - 11808

Published: Aug. 9, 2023

We report on a visible light-mediated cascade carbamoylation/cyclization of acrylamides using dihydropyridyl carbamoyl donors derived from alkyl amines. Diversely selected including 2-cyano-N-arylacrylamides, indolyl- and benzimidazolyl acrylamides, 2-alkynyl-N-aryl participate in this reaction, providing products good yields. The highlights photochemical method include the application amine-derived donors, peroxide-free reaction conditions, broad scope.

Language: Английский

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Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards synthesis of α- Amide Substituted Ether Derivatives

Synlett, Journal Year: 2024, Volume and Issue: 35(16), P. 1914 - 1918

Published: Feb. 20, 2024

Abstract Photoinduced carbamoylation of ethers using isocyanates as amide sources was accomplished under mild and environmentally friendly reaction conditions. A series were tolerated in this protocol to construct α-amide-substituted ether derivatives with desired yields. The method featured broad substrate scope good functional group tolerance, which could play an important role the construction biological molecules ethers.

Language: Английский

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1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2905 - 2905

Published: June 19, 2024

The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. then be further converted into fluoroalkylated α-fluoroalkylated diarylmethanes.

Language: Английский

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Metal-free photoinduced generation and alkynylation of carbamoyl radicals: a facile synthesis of alkynyl amides

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(71), P. 9582 - 9585

Published: Jan. 1, 2024

A metal-free photoinduced alkynylation of carbamoyl radicals with hypervalent iodine( iii ) reagents for a facile synthesis alkynyl amides has been developed.

Language: Английский

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A single-pot synthesis of 4-hydroxybenzophenones via acid-catalyzed alkoxylation of p-quinone methides followed by DDQ-assisted oxo-demethoxylation

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(39), P. 18419 - 18429

Published: Jan. 1, 2023

A single-pot, two-step approach has been established based on the alkoxylation of p-QMs using readily accessible Amberlyst-15 and DDQ-assisted oxo-demethoxylation to synthesize highly valuable 4-hydroxybenzophenones (81–99%) at room temperature.

Language: Английский

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