Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1821 - 1833

Published: Jan. 1, 2024

Metal-free synthesis of medicinally important carbamoylated dihydroquinolinones using readily available, cheap and environment-friendly materials with good to excellent yields.

Language: Английский

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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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Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 997 - 997

Published: Feb. 25, 2024

The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple practical method the synthesis amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through carbamoyl-radical-triggered cascade cyclization N3-alkenyl-tethered quinazolinones. Notably, carbamoyl radical generated in situ from oxidative decarboxylative process oxamic acids presence (NH4)2S2O8.

Language: Английский

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Generation of Carbamoyl Radicals and 3,4-Dihydroquinolin-2(1H)-ones Enabled by Iron Photoredox Catalysis

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: May 16, 2024

Abstract A new protocol for accessing 3,4-dihydroquinolin-2(1H)-ones was established through a sequence of iron-catalyzed photoredox generation carbamoyl radicals from oxamic acids, addition the to electron-deficient alkenes, intramolecular cyclization, and aromatization. The process is compatible with variety N-phenyloxamic acids monosubstituted, 1,1-disubstituted, trisubstituted alkenes. Employing cheap, readily available, environmentally benign iron as catalyst, provides an excellent alternative synthesis 3,4-dihydroquinolin-2(1H)-ones.

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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Visible-Light-Induced Three-Component Radical Coupling of Selenocarbamates, Enones, and Allylstannanes with Diphenyl (2,4,6-trimethylbenzoyl)phosphine Oxide

Synlett, Journal Year: 2023, Volume and Issue: unknown

Published: Nov. 20, 2023

Abstract A blue LED-induced three-component coupling of a carbamoyl radical, cyclic enone, and allylstannane was developed. The use LEDs diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) as radical initiator permitted the to proceed with high chemoselectivity. An elucidation mechanism revealed pathway for formation tributyltin from TPO allylstannane. This tandem reaction is expected be applicable in natural-product synthesis.

Language: Английский

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