Oxamic acids: useful precursors of carbamoyl radicals

Chemical Communications, Год журнала: 2022, Номер 58(55), С. 7593 - 7607

Опубликована: Янв. 1, 2022

Thermal, photochemical, or electrochemical-mediated decarboxylation of oxamic acids generate nucleophilic carbamoyl radicals, which react efficiently with unsaturated systems, but also amines, alcohols and thiols under oxidative conditions.

Язык: Английский

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Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(7)

Опубликована: Янв. 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.

Язык: Английский

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

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(9), С. 1821 - 1833

Опубликована: Янв. 1, 2024

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

Язык: Английский

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Urethanes synthesis from oxamic acids under electrochemical conditions

Chemical Communications, Год журнала: 2020, Номер 56(81), С. 12226 - 12229

Опубликована: Янв. 1, 2020

Electrochemical decarboxylation of oxamic acids in the presence alcohols provides urethanes.

Язык: Английский

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Persulfate promoted tandem radical cyclization of ortho-cyanoarylacrylamides with oxamic acids for construction of carbamoyl quinoline-2,4-diones under metal-free conditions

Chinese Chemical Letters, Год журнала: 2021, Номер 32(11), С. 3632 - 3635

Опубликована: Апрель 19, 2021

Язык: Английский

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Direct Minisci-Type C–H Amidation of Purine Bases

Organic Letters, Год журнала: 2022, Номер 24(43), С. 8008 - 8013

Опубликована: Окт. 26, 2022

A method for the C-H carboxyamidation of purines has been developed that is capable directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on were limited to alkylations arylations. Herein, we present first direct amidation a wide range purines: xanthine, guanine, adenine structures, including guanosine- adenosine-type nucleosides. The reaction also metal-free, cheap, operationally simple, scalable, applicable late-stage functionalizations biologically important molecules.

Язык: Английский

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Silver‐Catalyzed Decarboxylative Coupling of Oxamic Acids with Styrenes to Synthesize E‐Cinnamamides: A Distinguish Reaction Pathway

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

Abstract A silver‐catalyzed decarboxylative coupling of oxamic acids with styrenes has been developed to produce E ‐cinnamamides. Oxamic act as efficient precursors for carbamoy radicals. Based on the mechanistic experiments and intermediate analysis, proposed mechanism involves radical addition styrenes, followed by oxidation solvent participation, ultimately leading formation cinnamamides which is different from reported cases.

Язык: Английский

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Silver-catalysed C–H bond activation: a recent review

New Journal of Chemistry, Год журнала: 2021, Номер 45(35), С. 15718 - 15738

Опубликована: Янв. 1, 2021

Transition metal catalysed C–H activations are efficient, simple, mild, cost-effective and stereoselective, many of them environmentally sustainable transformations.

Язык: Английский

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Direct C–H aminocarbonylation ofN-heteroarenes with isocyanides under transition metal-free conditions

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(13), С. 2917 - 2922

Опубликована: Янв. 1, 2021

A C-C bond forming amide synthesis through direct C-H aminocarbonylation of N-heteroarenes with isocyanides was developed. The reaction mediated by an inorganic persulfate salt under transition metal-free conditions. Mechanistic studies suggested a radical pathway for this without the participation H2O and O2. This method also showed merits substrate availability, easy operation atom economy. It provided efficient route straightforward N-heteroaryl amides.

Язык: Английский

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Direct C–H Functionalization of Phenanthrolines: Metal- and Light-Free Dicarbamoylations

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 17282 - 17293

Опубликована: Ноя. 18, 2021

A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable directly installing primary, secondary as well tertiary amides. This a significant improvement on the previous method, was limited to primary The metal-, light-, and catalyst-free Minisci-type reaction cheap, operationally simple, scalable. We demonstrate that step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.

Язык: Английский

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