1153-66-8

Usage

Synthesis Reference(s)

Tetrahedron, 48, p. 1263, 1992 DOI: 10.1016/S0040-4020(01)90788-4

InChI:InChI=1/C15H23NO4/c1-6-11-12(14(17)19-7-2)9(4)16-10(5)13(11)15(18)20-8-3/h11,16H,6-8H2,1-5H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 123-38-6 propionaldehyde 
• 631-61-8 ammonium acetate 
• 506-87-6 ammonium carbonate 
• 626-34-6 ethyl aminocrotonate 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 113700-12-2 1-(1-Chloro-propyl)-pyridinium; chloride 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 

Downstream Products

• 27525-74-2 dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate 
• 18657-09-5 (E)-1-(but-1-en-1-yl)-4-methoxybenzene 
• 1609469-10-4 C₁₃H₁₇NO₄*HNO₂ 
• 1009-14-9 phenyl butyl ketone 
• 69687-78-1 3-ethyl-2,4-dimethyl-1H-pyrrole 

Relevant academic research and scientific papers

Thiamine hydrochloride-catalyzed one-pot synthesis of 1,4-dihydropyridine derivatives under solvent-free conditions

An efficient one-pot synthesis of 1,4-dihydropyridines from an aldehyde, β-keto ester, and ammonium acetate or formamidine acetate using thiamine hydrochloride (VB1) as the catalyst under solvent-free conditions at ambient temperature is described. All types of aldehydes, including aromatic, aliphatic, and unsaturated aldehydes, give good yields. The catalyst can easily be recovered after completion of the reaction and reused without affecting its activity.

Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis

An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.

A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature

A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.

Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex

The invention belongs to the technical field of catalytic organic synthesis, and particularly relates to a preparation method and application of a novel ionic beta-naphthol aldehyde Schiff base zirconium complex. Zirconium atoms are coordinated with a beta-naphthol aldehyde Schiff base ligand and water molecules, and two perfluoroalkyl (aryl) sulfonic acid groups are combined with central atom zirconium through covalent bonds and ionic bonds respectively. The preparation method comprises the following steps: dissolving beta-naphthol aldehyde Schiff base zirconium dichloride in a solvent, adding a silver salt under the protection of N2, reacting the mixture for 1-4 hours in a dark place at room temperature, performing filtration, adding n-hexane into filtrate until layering, putting the solution into a refrigerator, and freezing the solution for 24 hours to separate out the beta-naphthol aldehyde Schiff base zirconium complex. The beta-naphthol aldehyde Schiff base zirconium complex hashigh air stability and strong Lewis acidity, and can efficiently catalyze the Hantzsch reaction of aldehyde, beta-ketoester and ammonium acetate to synthesize 1,4-dihydropyridine derivatives.

MIL-101-SO3H metal-organic framework as a Br?nsted acid catalyst in Hantzsch reaction: An efficient and sustainable methodology for one-pot synthesis of 1,4-dihydropyridine

A straightforward and efficient methodology for the one-pot multicomponent synthesis of 1,4-dihydropyridine has been developed using MIL-101-SO3H metal-organic framework as a solid Br?nsted acid. The presence of the uniformly distributed Br?nsted acidic sulfonic acid sites throughout the framework and the high stability bestow the catalyst with excellent reactivity towards the synthesis of 1,4-dihydropyridine under simple reaction conditions using renewable ethanol as the solvent. The present methodology tolerates various functional groups and allows the synthesis of 1,4-dihydropyridine derivatives in good to excellent yields through Hantzsch reaction. The developed methodology proceeds under mild conditions, avoids corrosive reagents and special reaction conditions, and is amenable to gram scale synthesis. The sustainable nature of the catalyst was proved by the easy recovery and the reusability of the catalyst, as it was reused several times without loss in activity, which was confirmed from the FTIR, PXRD and SEM analyses of the reused catalyst.

Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines

An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising reagent and offers several advantages over other reported reagents in terms of reaction time and yields. The supported reagent is found to be more efficient and selective when compared with its unsupported form. The Belousov–Zhabotinskii reaction was not observed in present reaction. The dealkylation observed in case of 4-n-alkyl/n-alkenyl with other oxidising agents is also not observed in the present case.

A novel three-phenyl bismuth organic (V) complex catalyst and its preparation method and a nitrogen-containing compound in the synthesis of the catalytic application

The invention provides a novel triphenyl organic bismuth (V) complex catalyst I, a preparation method thereof, and a synthesis method for nitrogen-containing compounds II-V under the catalysis of the novel triphenyl organic bismuth (V) complex catalyst I. The complex I is a cation-type organic bismuth complex, and the molecular formula is Ph3BiX2 (X=OSO2C4F9, OSO2C6F5, OSO2C8F17). The bismuth atom in the complex is connected with three triphenyls to show pentavalence. The other two perfluorooctane sulfonate roots and the cation part of the complex form an ionic bond. The synthesis method is used for synthesizing four types nitrogen-containing compounds, including bis(indolyl)methane II, dihydropyrimidinone III, dihydropyridine IV and beta-alkamine V, by taking the triphenyl organic bismuth compound as a catalyst and a conventional organic solvent as a reaction solvent. The method has the advantages of lower cost, high yield, simplicity and convenience in operation, zero pollution, repeated use of the catalyst and the like, and creates a cheap and environment-friendly way for preparing the nitrogen-containing compounds.

Air-stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N-Containing Compounds

Triphenyl bismuth bisperfluorooctanesulfonate is an air- and water-stable Lewis acid. It exhibits high catalytic efficiency for the synthesis of nitrogen heterocycles such as diindolylmethane derivatives, dihydropyrimidinones, dihydropyridines and 1,2-disubstitued benzimidazoles under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles.This catalytic system affords a simple and efficient way for the synthesis of N-containing compounds.

Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase

1,4-Dihydropyridine-3,5-dicarboxylate derivatives (1-25) were synthesized in high yields via Hantzsch reaction and evaluated for their α-glucosidase inhibitory activity. Compounds 1, 2, 6-8, 11, 13-15, and 23-25 showed a potent inhibitory activity against yeast α-glucosidase with IC50 values in the range of 35.0-273.7 μM, when compared with the standard drug acarbose (IC50 = 937 ± 1.60 μM). Their structures were characterized by different spectroscopic techniques. The kinetics, selectivity, and toxicity studies on these compounds were also carried out. The kinetic studies on most active compounds 14 and 25 determined their modes of inhibition and dissociation constants Ki. Compound 14 was found to be a non-competitive inhibitor with Ki = 25.0 ± 0.06, while compound 25 was identified as a competitive inhibitor with Ki = 66.0 ± 0.07 μM.

Silica functionalized sulphonic acid coated with ionic liquid: An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridines under solvent-free conditions

Silica-supported sulphonic acid catalysts were prepared and coated with ionic liquid, and their catalytic activities were evaluated for the one-pot synthesis of 1,4-dihydropyridines. Different catalysts with an ionic liquid layer (SCILLs) have been prepared with a view to determine the most active catalyst. Silica sulphonic acid coated with [BMIM][PF6] was found to be the most active catalyst and can be recycled for several runs without the loss of significant activity. It was characterized using SEM, TEM, TGA and FTIR.