Enamines Research Articles

Synthesis and Anti‐inflammatory Activity of N‐(4, 6‐Dimethylpyridin‐2‐yl) β‐Ketoamides and Derivatives

A novel series of 6-amino-2, 4-lutidine (6-AL) derivatives were synthesized and evaluated for anti-inflammatory activity. Starting from the pharmacophoric β-ketoamide grouping present in oxicams, we prepared the N-(4, 6-dimethylpyridin-2-yl) acetoacetamide (4), via acylation of 6-AL by a lactone, the benzoylacetamide (5) by aminolysis of ethyl benzoylacetate, and carbox-amides 6–9 issued from methyl 1-oxotetralin-2-carboxylates. Anti-inflammatory activity was determined by the inhibition of oedema in carrageenan-induced rat paw oedema. Although acetoacetamide 4 proved less potent than the 3-fluorobenzamide 1, transformation into its enamine prodrug derivative 12 conferred high inhibitory activity.

Imines, enamines and oximes

Covering: January 1997 to December 1998Continuing the coverage in Contemp. Org. Synth., 1997, 4, 517 p

Preparation of Enamines from the Condensation of Glycine Esters with Nitro-Heterocyclic Aldehydes

Preparation of Enamines from the Condensation of Glycine Esters with Nitro-Heterocyclic Aldehydes

1,4-N,C-elimination of trialkylsilanol as a new way of fragmentation ofN,N-bis(trialkylsilyloxy)enamines

1,4-N,C-elimination of trialkylsilanol as a new way of fragmentation ofN,N-bis(trialkylsilyloxy)enamines

Novel Synthesis of 2-Cyanoindan-1-one Enamines

A novel method is described for conversion of indan-1-one into enamines of 2-cyanoindan-1-one and thence to 10-amino-11H-indeno[1,2-b] quinolines (11).

Synthesis of unsymmetrical pyrazines by reaction of an oxadiazinone with enamines

Synthesis of unsymmetrical pyrazines by reaction of an oxadiazinone with enamines

Polyfunctionalized 3-nitropyridine derivatives by [4 + 2] cycloadditions of 4-nitro-3-phenylisoxazole-5-carboxylates with enamines: applications and limits

Polyfunctionalized 3-nitropyridine derivatives by [4 + 2] cycloadditions of 4-nitro-3-phenylisoxazole-5-carboxylates with enamines: applications and limits

ChemInform Abstract: Preparation and 3‐Aza‐Cope Rearrangement of N‐Alkyl‐N‐allyl Enamines.

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Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines

Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines

Facile Synthesis of Selectively Monoprotected Unsymmetrical 1,3-Diketones from 2,2-Dimethoxyethyl Esters

Abstract Selectively monoprotected unsymmetrical 1,3-diketones were obtained by the reaction of 2,2-dimethoxyethyl esters with enamines in the presence of dichlorobis(trifiuoro-methanesulfonato)titanium.

A New Synthesis of 1-(Trifluoromethyl)enamines and 1- (Trifluoromethyl)alkylamines

Several 1-(trifluoromethyl)enamines were prepared by heating trifluoroacetamides with alkylidenetriphenylphosphoranes in THF or benzene. The product enamines can be reduced (H2, Pd/C) to 1-(trifluoromethyl)alkylamines.

Phase-Transfer Catalysed Alkylation of Enamines of some Cyclic β-Keto Carbothionic Acid Anilides with 1,2-Dibromoethane. Synthesis of Enamines of 1-Oxo-2-(3-phenyl tetrahydrothiazol-2-ylidene)-cycloalkanes

The alkylation of morpholine enam ines of 2-oxo-cycloalkane-1-carbothionic acid anilides (1-3) with 1,2-dibromoethane under phase-transfer catalytic conditions yields enam ines of 1-oxo-2-(3-phenyl-tetrahydrothiazol-2-ylidene)-cycloalkanes (4-6). Compounds 4-6 were hydrolysed to appropriate keto derivatives 8-10. The structure of obtained com pounds was established on the basis of IR. NM R and MS spectral data.

ChemInform Abstract: 1,5‐Dicarbonyl Compounds via Michael‐Addition of Deprotonated Enamines and Allylamines to 2‐(N‐Methylanilino)acrylonitrile.

AbstractCoupling of the anions (I), obtained from enamines or allylamines by metalation, with 2‐(N‐methylanilino)acrylonitrile (II), followed by alkylation and hydrolysis, yields the 1,5‐dicarbonyl compounds (VI) via the aminocyanoenamines (V) (R1: ‐Ph).

The Phosphorylated Enamines

Abstract The primary phosphorylated enamines were obtained by aminomethylenation of the phosphorus-containing CH-acids with bis-silylformamide.

ChemInform Abstract: Annulation of 2‐Formyl‐2‐cyclohexenones by Reaction with Enamines.

AbstractAus den 2‐Formyl‐cyclohexenonen (I) erhält man mit dem Enamin (II) unter sauren Bedingungen die Addukte (III) und (IV), die mit Trifluoressigsäure zu den Octalindionen (V) dehydratisiert werden.

ChemInform Abstract: Synthesis of Simple Enamino Thioaldehydes.

AbstractDie Enamine (I) werden in ihre Vilsmeier‐Salze übergeführt, die bei der in situ‐Solvolyse mit NaHS die kristallinen ungesättigten Thioaldehyde (II) ergeben.

Optimization in Organic Synthesis. Strategies When the Desired Reaction is Accompanied by Parasitic Side Reactions. An Example with Enamine Synthesis.

On propose 3 methodes assistees par ordinateur. Application a l'optimisation de la synthese, catalysee par TiCl 4 de l'enamine de la morpholine, dimethyl-2',2' methylene-1' propyl-4 morpholine, par reaction avec la pinacolone

Annulation of 2-formyl-2-cyclohexenones by reaction with enamines

3-Methyl-2-pyrrolidino-1-butene reacts with a series of 2-formyl-2-cyclohexen-ones to give mixtures of 7,7-dimethyl-Δ 8-octalin-1,6-diones and 7,7-dimethyl-8-hydroxy- trans -decalin-1,6-diones which are dehydrated by TFA to afford the octalindiones in overall yields of 80% or better; annulation is >95% diastereoselective with 4-monosubstituted formyl enones.

Construction of linear-fused tricyclopentanoids by intramolecular [6 + 2] cycloadditions of fulvenes with enamines

Construction of linear-fused tricyclopentanoids by intramolecular [6 + 2] cycloadditions of fulvenes with enamines

Synthesis of simple enamino thioaldehydes

Simple enamino thioaldehydes (1)–(5) are synthesised by the thioformylation of alicyclic enamines.