15768-07-7

Usage

InChI:InChI=1/C12H12O3/c1-9(13)11(12(14)15-2)8-10-6-4-3-5-7-10/h3-8H,1-2H3/b11-8-

Upstream product

• 100-52-7 benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 141-97-9 ethyl acetoacetate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 150016-65-2 (3Z)-3-iodo-4-phenylbut-3-en-2-one 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 98-86-2 acetophenone 
• 23326-27-4 Methyl 2-butynoate 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 108817-72-7 2,5-dimethyl-3-phenyl-4-carbomethoxy-4-isoxazoline 

Downstream Products

• 111556-83-3 isobutyl methyl 1,4-dihydro-2,6-dimethyl-4-phenyl-3,5-pyridinedicarboxylate 
• 142592-01-6 1,5-dimethoxycarbonyl-2-methyl-4-morpholino-6-phenyl-1,3-cyclohexadiene 
• 118432-12-5 3-Cyclopentyl-1,6-dimethyl-4-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester; hydrochloride 
• 123207-09-0 3,3-Dimethoxy-2-[1-phenyl-meth-(Z)-ylidene]-butyric acid methyl ester 
• 80742-11-6 6-Methyl-2,4-bis-(2-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-5-carbonsaeuremethylester 
• 80742-11-6 6-Methyl-2,4-bis-(2-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-5-carbonsaeuremethylester 
• 121725-72-2 2-acetyl-3-phenyl-pent-4-enoic acid methyl ester 
• 312266-61-8 6-amino-2,4-dihydro-3-methyl-4-phenylpyrano[2,3-c]pyrazole-5-carbonitrile 
• 133488-55-8 6-Amino-1,4-dihydro-2-methyl-5-nitro-4-phenyl-nicotinsaeuremethylester 

Relevant academic research and scientific papers

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds

In the present work, we report the catalytic reaction of active methylene compounds with cyclic enol ethers and aryl acetals through oxonium intermediate under solvent-free conditions using heterogeneous solid acid catalysts. Among studied solid acid catalysts, Amberlyst-15 gave excellent yields (35–85%) of alkylated products. The catalyst showed broader substrate scope, and a recyclable catalytic cost-efficient approach of the alkylation was examined on the different types of cyclic enol ethers and aryl acetal.

Cross-linked polystyrene-TiCl4 complex as a reusable Lewis acid catalyst for solvent-free Knoevenagel condensations of 1,3-dicarbonyl compounds with aldehydes

Cross-linked polystyrene copolymer beads with the average particle size in the range of (50–80 mesh size) were prepared by a new method, characterized and functionalized with titanium tetrachloride to afford the corresponding polystyrene?titanium tetrachloride complex in one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This polymer metal complex (PS/TiCl4) was used as a heterogeneous, recoverable, reusable Lewis acid for solvent-free Knoevenagel condensations of 1,3-diketones with aromatic aldehydes under green and mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. This complex showed good stability and catalytic activity in the Knoevenagel reactions.

Microwave Oriented Solid Support Synthesis of Novel 5,6-Disubstituted-1,2,4-Triazolopyrimidines as Antifungal Agents

Microwave oriented, basic solid support assisted, two-step reaction of aryl aldehyde, active methylene compounds, and 3-amino-1,2,4-triazole yielded 5,6-disubstituted-1,2,4-triazolopyrimidines in excellent yield without side products, in short reaction time. The preliminary in vitro antifungal evaluation of the compounds indicated the promising antifungal potential of the synthesized compounds against most of the test fungi using standard fungicides as a positive control. The in silico analysis of the synthesized molecules favors the results of in vitro analysis.

Design and synthesis of orally bioavailable 4-methyl heteroaryldihydropyrimidine based hepatitis B virus (HBV) capsid inhibitors

Targeting the capsid protein of hepatitis B virus (HBV) and thus interrupting normal capsid formation have been an attractive approach to block the replication of HBV viruses. We carried out multidimensional structural optimizations based on the heteroaryldihydropyrimidine (HAP) analogue Bay41-4109 (1) and identified a novel series of HBV capsid inhibitors that demonstrated promising cellular selectivity indexes, metabolic stabilities, and in vitro safety profiles. Herein we disclose the design, synthesis, structureactivity relationship (SAR), cocrystal structure in complex with HBV capsid proteins and in vivo pharmacological study of the 4-methyl HAP analogues. In particular, the (2S,4S)-4,4-difluoroproline substituted analogue 34a demonstrated high oral bioavailability and liver exposure and achieved over 2 log viral load reduction in a hydrodynamic injected (HDI) HBV mouse model.

Indium(III)-catalyzed knoevenagel condensation of aldehydes and activated methylenes using acetic anhydride as a promoter

The combination of a catalytic amount of InCl3 and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic aldehydes, conjugate aldehydes, and aliphatic aldehydes. Central to successfully driving the condensation series is the formation of a geminal diacetate intermediate, which was generated in situ from an aldehyde and an acid anhydride with the assistance of an indium catalyst.

Improving the selectivity toward three-component biginelli versus hantzsch reactions by controlling the catalyst hydrophobic/hydrophilic surface balance

The catalytic activities and selectivities of two kinds of mesoporous solid acids SBA-15-PrSO3H 1, SBA-15-Ph-PrSO3H 2, and a periodic mesoporous organosilica (PMO) based solid acid Et-PMO-Me-PrSO3H 3 that comprise differen

Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst

In this study, a green, simple and efficient method for the preparation of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c] pyrazoles by means of a one-pot four component condensation reaction of aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate is reported. The reaction utilizes isonicotinic acid as a dual and biological organocatalyst at 85 °C under solvent-free conditions.

Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol

The synthesis of a large number of β-and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were

Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines

New strategies for the oxidative cycloaddition of enones with enamines are developed. These cycloaddition reactions directly afford substituted aromatic amines, which are important in organic chemistry, in moderate to good yield. Cu(OAc)2/TFA is shown to be essential to achieve high reaction efficiency.