Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy

Joly, Nicolas; Bettoni, Léo; Gaillard, Sylvain; Poater, Albert; Renaud, Jean‐Luc

doi:10.1021/acs.joc.1c00654

Cited by 20 publications

(13 citation statements)

References 48 publications

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“…On the basis of the results of our experiments and previous reports, − , we propose a plausible reaction mechanism for the transformation of dialkylation of acyl hydrazide (Scheme ).…”

Section: Resultssupporting

confidence: 71%

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N,N-Dialkylation of Acyl Hydrazides with Alcohols Catalyzed by Amidato Iridium Complexes via Borrowing Hydrogen

et al. 2023

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Direct N,N-dialkylation of acyl hydrazide catalyzed by a series of amidato iridium complexes bearing an electron-donating group in the ligand using methanol or ethanol as the alkyl reagent under weak base conditions (10 mol % KHCO 3 ) is described. A wide range of acyl hydrazide derivatives are converted to the corresponding N,N-dialkylated products in excellent yields (38 examples, yields of ≤96%). On the basis of the control experiments and nuclear magnetic resonance studies, a plausible mechanism was proposed. The experimental results indicate that ortho electron-donating groups on the phenyl moiety of the picolinamide ligand play a crucial role in catalytic activity.

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“…On the basis of the results of our experiments and previous reports, − , we propose a plausible reaction mechanism for the transformation of dialkylation of acyl hydrazide (Scheme ).…”

Section: Resultssupporting

confidence: 71%

“…Most recently, Renaud et al. developed a series of ruthenium tricarbonyl complexes bearing a diaminocyclopentadienone ligand for the synthesis of monoalkyl, dialkyl, and nonsymmetric N,N- dialkyl acyl hydrazides in the presence of a stoichiometric amount of NaO t Bu and additive Me 3 NO (Scheme b, Previous Work). , …”

Section: Introductionmentioning

confidence: 99%

N,N-Dialkylation of Acyl Hydrazides with Alcohols Catalyzed by Amidato Iridium Complexes via Borrowing Hydrogen

et al. 2023

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“…A variety of primary as well as secondary alcohols were introduced in this alkylation and afforded mono‐ and dialkylated acyl hydrazides in moderate to good yields (Scheme 1). [13b] But, to date, there is no tandem and/or multicomponent alkylation of hydrazine derivatives with two different alcohols.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium‐Catalyzed Three‐Component Alkylation: A Tandem Approach to the Synthesis of Nonsymmetric N,N‐Dialkyl Acyl Hydrazides with Alcohols

et al. 2021

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The borrowing hydrogen strategy has been applied in the synthesis of nonsymmetric N,N‐dialkylated acyl hydrazides via a tandem three‐component reaction catalyzed by a phosphine free diaminocyclopentadienone ruthenium tricarbonyl complex. This strategy represents the first direct one‐pot approach to nonsymmetric functionalized acyl hydrazides. Different aromatic acyl hydrazides underwent dialkylation with a variety of primary or secondary alcohols and methanol or ethanol as alkylating agents in mild reaction conditions and good yields. Deuterium labelling experiments suggested that the primary or secondary alcohol was the hydrogen source in this tandem process. DFT calculations show that the combination of the tandem mixed product cannot be perfectly explained neither structurally nor electronically, but might be dependent of the physical state of the aldehyde or ketone intermediate (gaz vs. liquid) at the reaction temperature.

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“…Furan-2-carbohydrazide 1 [57] and 4-aryl-2,4dioxobutanoic acids 2a-e [58,59] were prepared according to the literature methods.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

et al. 2022

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New methyl 5-aryl-1-(furan-2-carbonyl)-1H-pyrazole-3-carboxylates were obtained via decyclization reaction of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides under the action of methanol. Starting N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides were obtained by intramolecular cyclization of substituted 4-aryl-2-[2-(furan-2-ylcarbonyl)hydrazinylidene]-4-oxobutanoic acids in propionic anhydride. The structure of the compounds obtained was confirmed by the 1H NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of some obtained compounds was studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection.

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Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy

Cited by 20 publications

References 48 publications

N,N-Dialkylation of Acyl Hydrazides with Alcohols Catalyzed by Amidato Iridium Complexes via Borrowing Hydrogen

N,N-Dialkylation of Acyl Hydrazides with Alcohols Catalyzed by Amidato Iridium Complexes via Borrowing Hydrogen

Ruthenium‐Catalyzed Three‐Component Alkylation: A Tandem Approach to the Synthesis of Nonsymmetric N,N‐Dialkyl Acyl Hydrazides with Alcohols

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

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