Lower primary alkanols and their esters in a Ritter-type reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides

Lebedev, Mikhail Y.; Érman, M. B.

doi:10.1016/s0040-4039(02)00057-6

Cited by 24 publications

(7 citation statements)

References 8 publications

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“…With the cyano group in the axial position, proton abstraction is highly disfavoured and rather drastic conditions are required for epimerization to occur. Microwave irradiation at 160°C over a period of 20 min in 0.1  NaOEt in ethanol afforded a 1:1 mixture of the epimers 4a and 4b, [18] which could not be separated by chromatography (Scheme 3).…”

Section: Preparation Of Ligandsmentioning

confidence: 99%

Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach

2003

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Chiral arylated pyridyl alcohols, pyridyl phosphinites and pyridyl phosphites were prepared by Suzuki arylation and/or O-functionalization with a chlorodiarylphosphane or a chlorodiarylphosphite of chiral 2-bromo-6-(1-hydroxyalkyl)pyridines or 2-(1-hydroxyalkyl)pyridines, with the chirality originating from the chiral pool. The pyridyl alcohols were assessed as catalysts for the addition of diethylzinc to benzaldehyde and the P,N-ligands were employed in the palla-

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Section: Preparation Of Ligandsmentioning

confidence: 99%

Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach

2003

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“…The Ritter reaction, which is the reaction of alcohols with nitriles, is one method of producing amides [1][2][3][4][5] . However, the catalysts used in this reaction are generally strong acids or heavy-metal compounds, which are very expensive and/or toxic.…”

Section: Introductionmentioning

confidence: 99%

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

et al. 2010

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“…Finally,b ecause these newly synthesized compounds bear a chiral carbon atom at the 4-position, an attemptw as made to separate the two enantiomers of one racemic 2,2-dimethylchroman compound (to obtain (+)-and (À)-29)a nd to examine potentiald ifferences in their biological activities (inhibition of insulin release and vascular smoothm usclerelaxation). The key intermediate 6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol (27), obtained as previously described, [20] was treated with cuprous cyanidei n1 -methyl-2-pyrrolidinone to provide the 6-cyano-substituted intermediate 28 (Scheme 2). The latter compound was converted into the corresponding 4-acetamido-substituted target compound 13 under the conditions of the Ritter reaction [27] (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

“…The key intermediate 6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol (27), obtained as previously described, [20] was treated with cuprous cyanidei n1 -methyl-2-pyrrolidinone to provide the 6-cyano-substituted intermediate 28 (Scheme 2). The latter compound was converted into the corresponding 4-acetamido-substituted target compound 13 under the conditions of the Ritter reaction [27] (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Deciphering Structure–Activity Relationships in a Series of 2,2‐Dimethylchromans Acting as Inhibitors of Insulin Release and Smooth Muscle Relaxants

et al. 2017

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4,6-Disubstituted 2,2-dimethylchromans are reported as pharmacologically active compounds that mainly target the ATP-sensitive potassium channels. The present study is an attempt to characterize the impact of the nature of substituents introduced at the 4- and 6-positions of 2,2-dimethylchromans on their capacities to inhibit insulin release from pancreatic β-cells or to relax vascular smooth muscle cells, both biological responses that are supposed to reflect interaction with specific ion channels. From the core structure 4-amino-2,2-dimethylchroman, a progressive increase in the steric hindrance of the chemical functionalities introduced at the 4-position (amino, formamido, acetamido, arylureido/thioureido) and at the 6-position (amino, formamido, acetamido, alkoxycarbonylamino) led to a progressive magnification of the inhibitory effect on the insulin release process and, to a lesser extent, of the vasorelaxant activity. Moreover, the dextrorotatory enantiomer of 2,2-dimethylchroman compound 29 was more potent than its levorotatory counterpart for inhibiting the insulin secretory process. Additional pharmacological investigations suggested, however, that the myorelaxant activity of 11 and 15 resulted from a direct Ca entry blockade.

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Lower primary alkanols and their esters in a Ritter-type reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides

Cited by 24 publications

References 8 publications

Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach

Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

Deciphering Structure–Activity Relationships in a Series of 2,2‐Dimethylchromans Acting as Inhibitors of Insulin Release and Smooth Muscle Relaxants

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