10412-92-7

Upstream product

• 10472-13-6 2-benzylamino-2-hydroxy-cyclopentanecarboxylic acid ethyl ester 
• 71-43-2 benzene 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Expanding dynamic kinetic protocols: Transaminase-catalyzed synthesis of α-substituted β-amino ester derivatives

Several α-alkylated β-amino esters have been obtained via DKR processes employing a kit of transaminases and isopropylamine as an amino donor in aqueous medium under mild conditions. Thus, while acyclic α-alkyl-β-keto esters afforded excellent conversions and enantioselectivities, although usually low diastereoselectivities, using more constrained cyclic β-keto esters high to excellent inductions were obtained.

A Convenient and Effective Method for Synthesizing β-Amino-α ,β-Unsaturated Esters and Ketones

A convenient and effective method for the preparation of β-amino-α, β-unsaturated esters and ketones has been developed through silica gel-catalyzed and solvent-free reactions of β-dicarbonylic compounds with ammonia and primary amines.

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.

Visible Light Promoted β-C—H Alkylation of β-Ketocarbonyls via a β-Enaminyl Radical Intermediate

A 5πe carbonyl activation mode is reported on the basis of photo-induced single-electron-transfer (SET) oxidation of a secondary enamine. The resultant β-enaminyl radical intermediate was trapped by a wide range of Michael acceptors, producing β-alkylation products of β-ketocarbonyls in a highly efficient manner.

Assembly of four diverse heterocyclic libraries enabled by prins cyclization, Au-catalyzed enyne cycloisomerization, and automated amide synthesis

We describe a unified synthetic strategy for efficient assembly of four new heterocyclic libraries. The synthesis began by creating a range of structurally diverse pyrrolidinones or piperidinones. Such compounds were obtained in a simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by providing rapid entry into a wide range of bicyclic and tricyclic dienamides. The final stage of the process entailed diversification of each of the initially produced carboxylic acids using a fully automated platform for amide synthesis, which delivered 1872 compounds in high diastereomeric and chemical purity.

General, mild and efficient synthesis of β-enaminones catalyzed by ceric ammonium nitrate

Ceric ammonium nitrate catalyzes the reaction between aromatic or aliphatic primary amines and a variety of β-dicarbonyl compounds, including β-ketoesters, β-ketothioesters and β-diketones. The reaction proceeds smoothly at room temperature in short react

Ketones in the catalytic three-component "one-pot" Kabachnik - Fields synthesis of α-amino phosphonates

Reactions of carbocyclic, heterocyclic, and steroidal ketones with benzylamine and diethyl phosphite in a catalytic three-component "one-pot" synthesis of α-amino phosphonates were studied. The activities of mono-and binuclear complexes of tetra(tert-butyl)phthalocyanines as catalysts for this process were compared. Springer Science+Business Media, Inc. 2006.

Regio- and stereoselective double alkylation of β-enamino esters with organolithium reagents followed by one-pot reduction: convenient method for the synthesis of tertiary γ-amino alcohols

An easy, high yielding and stereoselective procedure for the preparation of tertiary γ-amino alcohols starting from β-enamino esters is presented. In this procedure, the double alkylation of β-enamino esters with organolithium reagents is followed by one-

Efficient synthesis of β-aminoacrylates and β-enaminones catalyzed by Zn(OAc)2·2H2O

The direct condensation of amines with β-ketoesters and β-diketones to produce functional enamine derivatives has been investigated with zinc Lewis acid catalysts. Zn(OAc)2·2H2O shows good catalytic activity and leads to a chemo- and stereoselective formation of (Z)-enamine derivatives from aliphatic primary amines and ring-substituted anilines under mild conditions.

Multiple pathways in the synthesis of new annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (emivirine)

Condensation of 3-(3,5-dimethylphenyl)-2-oxocyclopentanecarboxamide (11) with oxalyl chloride and condensation of ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate (17a) with trimethylsilyl isothiocyanate gave 7-(3,5-dimethylphenyl)-6,7-dihydro-5H-cyclopenta[e][1,3]oxazine-2,4-dione (12) and 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7-hexahydrocyclopentapyrimidin-4-o ne (18a), respectively. Acid catalyzed ring-closure of 6-(4-methyl-1-phenylpent-3-enyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (26) and radical mediated ring-closure of 1,3-bis(benzyloxymethyl)-5-bromo-6-(1-phenylbut-3-enyl)-1H-pyrimidine-2,4-dione (32a) gave 5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dione (28) and 1,3-bis(benzyloxymethyl)-5-methyl-7-phenyl-1,5,6,7-tetrahydrocyclopentapyrimidin e-2,4-dione (33), respectively. Annelated emivirine analogues 7-(3,5-dimethylphenyl)-1-ethoxymethyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4 -dione (4), 1-ethoxymethyl-5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dione (5) and 1-ethoxymethyl-5-methyl-7-phenyl-1,5,6,7-tetrahydrocyclopnetapyrimidine-2,4-dion e (6) were obtained in few steps from 12, 28 and 18a/33, respectively. These new analogues can be considered as conformationally locked analogues of emivirine. However, the compounds 4-6 showed lower activities against HIV-1 than emivirine and it is concluded that the locked conformation disfavours activity against HIV-1.