A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

Théodorou, Vassiliki; Paraskevopoulos, Georgios; Skobridis, Konstantinos

doi:10.3998/ark.5550190.p009.205

Cited by 23 publications

(11 citation statements)

References 24 publications

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“…Using aqueous sodium hydroxide, only non-separable mixtures of compounds were obtained. The same results were obtained using non-aqueous conditions, 14 or using sodium peroxide as a mild hydrolysing agent. 15 On the other hand, we were successful in reducing ketone 8d.…”

Section: © Author(s)supporting

confidence: 76%

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Klásek¹,

Lyčka²,

Rouchal³

2020

Arkivoc

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3-Chloroquinoline-2,4-diones react with ethanolamine to give 3-hydroxyethylaminoquinoline-2,4-diones. By reacting with isothiocyanic acid, these compounds cyclize to form thioxoimidazo derivatives. If a benzyl group is attached to carbon atom C-3, it is cleaved off. Simultaneously, molecular rearrangement proceeds through the formation of compounds with quinazoline skeletons. However, when using ethylene diamine, the compounds are subject to new types of molecular rearrangement leading to the formation of new quinazoline derivatives.

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Section: © Author(s)supporting

confidence: 76%

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

Klásek¹,

Lyčka²,

Rouchal³

2020

Arkivoc

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“…Finally, a non-optimized removal of the 5-methoxy-8amoinoquinoline directing group was performed in mild conditions [27] to provide the corresponding trifluoromethylselenolated acid 13 k (Scheme 7).…”

Section: Resultsmentioning

confidence: 99%

Aromatic Trifluoromethylselenolation via Pd‐catalyzed C−H functionalization

Grollier

Chefdeville

Jeanneau

et al. 2021

Chemistry A European J

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The synthesis of trifluoromethylselenolated aromatic molecules via an auxiliary-assisted, palladium catalyzed, CÀ H bonds functionalization with trifluoromethyl tolueneselenosulfonate as reagent is described. The mono-or bis-products can be preferentially formed. Some mechanistic investigations were realized to better understand the reaction. This methodology was also extended to fluoroalkylselenyl groups.

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“…A plausible mechanistic process was proposed 9,10 based on the well-established observation that hydroxide anions, when poorly solvated, attack the carbonyl groups of the esters or of the amides much more easily than the ordinarily strongly-solvated hydroxyl anions in an aqueous environment.…”

Section: Scheme 1 Alkaline Hydrolysis Of Esters and Amides And Hydration Of Nitriles In Non-aqueous Conditionsmentioning

confidence: 99%

“…In a previous work, we reported the alkaline hydrolysis of esters in non-aqueous reaction medium under very mild conditions, 9 including short reaction times at room temperature, and the use of a low concentration of alkali in MeOH/CH2Cl2 (1:9) as a solvent. We have also developed a mild protocol for the alkaline hydrolysis of secondary and tertiary amides 10 to the corresponding acids and amines, while nitriles are converted to primary amides (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%