76943-79-8

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 3332-08-9 2-isopropyliminopropane 
• 4111-54-0 lithium diisopropyl amide 
• 119-61-9 benzophenone 
• 75-31-0 isopropylamine 
• 93-91-4 1-phenylbutan-1,3-dione 
• 34075-91-7 benzoylacetonatoboron difluoride 
• 108-18-9 diisopropylamine 

Downstream Products

• 92267-79-3 [SnCl₄(C₆H₅COCHC(CH₃)NHCH(CH₃)2)2] 
• 92280-72-3 [SnI₄(C₆H₅COCHC(CH₃)NHCH(CH₃)2)2] 
• 143889-67-2 1,5-diphenyl-3-(N-isopropylamino)-6-cyanohex-2-en-1-one 
• 143889-52-5 6-(3-chloropropyl)-N-isopropyl-2-phenyl-4-pyridinamine 
• 143889-51-4 N-isopropyl-2-(3-methoxyphenyl)-6-phenyl-4-pyridinamine 
• 143889-58-1 2,6-bis(3-methoxyphenyl)-4-(1-hydroxystyr-2-yl)pyrimidine 
• 143889-50-3 2-(4-bromophenyl)-N-isopropyl-6-phenyl-4-pyridinamine 
• 143889-48-9 2,6-diphenyl-N-isopropyl-4-pyridinamine 
• 24334-85-8 3-Methyl-5-phenyl-isoxazol 
• 56426-41-6 3-methyl-5-phenylpyrazole 

Relevant academic research and scientific papers

Redox Property of Enamines

Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.

One-pot formation of aza-enolates from secondary amines and condensation to esters and alkyl bromides

Starting from commercial secondary amines, a one-pot procedure allows a direct access to enaminones through a one-pot deprotonation/oxidation/in situ re-deprotonation/acylation sequence without intermediate isolation of the intermediate Schiff base or its corresponding enamine tautomer. An alternative one-pot sequence involving a similar oxidation step followed by one or two alkylation steps yields, after acidic work-up, functionalized ketones directly from the parent amine. This process has been applied to an expeditious synthesis of the male aggregation pheromone of the cereal leaf beetle Oulema melanopus.

A new and a convenient route to enaminones and pyrazoles

A new method has been developed for the regioselective preparation of enaminones and pyrazoles from 1,3-diketonatoboron difluorides. The reactions proceed smoothly under mild reaction conditions, producing enaminones and pyrazoles in high yields.

The use of K-10/ultrasound in the selective synthesis of unsymmetrical β-enamino ketones

p-Phenyl substituted β-enamino ketones 2a-p and cyclic β-enamino ketones 4, 6a-f have been prepared by a selective method by dispersing 1,3- diketones and amines on montmorillonite K-10 under sonication.

An efficient, scaleable procedure for the conversion of esters to isoxazoles

A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.

Two Unexpected but Understandable Reactions with Lithium Diisopropylamide (LDA)

On treatment with LDA, the acylated oxazolidinones 3 and 10 gave the N-vinylamides 6, 7 and 11 in low yields.The esters 13, on treatment with an excess of LDA at 0 degC, gave a low yield of the β-aminovinyl ketones 15 in addition to the enolates.Methyl benzoate similarly gave the β-aminovinyl ketone 17.Neither the formation of the N-vinylamides nor of the β-aminovinyl ketones was easily made high yielding.

Reactivity of Imine Anions with Esters: A General Method for the Synthesis of Enamino Ketones

The reaction of α-metalated imines with esters under mild conditions leads to the Schiff base of unsymmetrical 1,3-diketones (enamino ketones) in good yield.