24393-47-3

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 4230-93-7 3,4-dimethoxynitrostyrene 

Downstream Products

• 38175-27-8 (3,4-dimethoxy-phenyl)-succinic acid 
• 38175-31-4 (+/-)-3-(3,4-dimethoxyphenyl)pyrrolidine 
• 153718-53-7 1-acetamido-4-amino-2-(3,4-dimethoxyphenyl)butane 
• 153718-52-6 4-acetamido-3-(3,4-dimethoxyphenyl)butyronitrile 
• 1195641-91-8 (Z)-3,4-dimethoxybenzaldehyde oxime 
• 401464-02-6 ethyl 2-amino-7-hydroxy-4-(3,4-dimethoxyphenyl)-4H-chromene-3-carboxylate 
• 6286-49-3 2-(3,4-dimethoxyphenyl)succinonitrile 

Relevant academic research and scientific papers

An intriguing case of the retro-Michael reaction

In the course of Michael addition of carbanions, derived from malononitrile or cyanoacetic ester, to a nitrostyrol retro reaction has also been observed. Depending on the reaction conditions any of the two compounds formed can be obtained as main product.

Optimisation of estrogen receptor subtype-selectivity of a 4-Aryl-4H-chromene scaffold previously identified by virtual screening

4-Aryl-4H-Chromene derivatives have been previously shown to exhibit anti-proliferative, apoptotic and anti-angiogenic activity in a variety of tumor models in vitro and in vivo generally via activation of caspases through inhibition of tubulin polymerisation. We have previously identified by Virtual Screening (VS) a 4-aryl-4H-chromene scaffold, of which two examples were shown to bind Estrogen Receptor α and β with low nanomolar affinity and 20-fold selectivity for α over β and low micromolar anti-proliferative activity in the MCF-7 cell line. Thus, using the 4-aryl-4H-chromene scaffold as a starting point, a series of compounds with a range of basic arylethers at C-4 and modifications at the C3-ester substituent of the benzopyran ring were synthesised, producing some potent ER antagonists in the MCF-7 cell line which were highly selective for ERα (compound 35; 350-fold selectivity) or ERβ (compound 42; 170-fold selectivity).

Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase

Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality.

Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes

A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.

Silica grafted polyethylenimine as heterogeneous catalyst for condensation reactions

Primary amine groups were attached to a silica surface by using α,ω-diamines derivatives and (3-glycidyloxypropyl)-trimethoxysilane activation. The same activation was used to graft polyethylenimine, which also contains secondary and tertiary amine groups. These silica aminated structures were tested as heterogeneous catalysts in nitroaldol condensation with nitromethane, the derivative with the polyethylenimine moiety being the more active catalyst. This catalyst also showed efficiency in the Knoevenagel condensation of benzaldehydes with ethyl cyanoacetate under very mild reaction conditions and showed much the same efficiency when used in consecutive reaction runs. A reaction mechanism with participation of the several amine groups of the catalysts is discussed.

First example of organocatalysis by polystyrene-supported PAMAM dendrimers: Highly efficient and reusable catalyst for knoevenagel condensations

This paper describes the first use of polystyrene-supported poly(amidoamine) (PAMAM) dendrimers as heterogeneous basic organocatalysts for carbon-carbon bond formation. Polystyrene-supported PAMAM dendrimers of first, second and third generations have been used as reusable base catalysts in Knoevenagel condensations of carbonyl compounds with active methylene compounds. The reactions proceed in short periods of time and with 100% selectivity. This novel catalyst eliminates the use of aromatic and halogenated solvents, as well as complex purification processes. The catalysts can be recycled ten times. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

One-pot formation of functionalised 2-piperidinones from arylidenecyanoacetates and methanolic ammonia via tandem reactions

Aryl aldehydes react with ethyl cyanoacetate in methanolic ammonium acetate to expeditiously furnish, besides high yields of arylidenecyanoacetates, 4,6-diaryl-3,5-dicyano-5-ethoxycarbonyl-2-piperidinonesinlow yields. But preformed arylidenecyanoacetates

Microwave-assisted Knoevenagel condensation of ethyl cyanoacetate with aldehydes in solvent-free condition

Piperazine has been used successfully as a catalyst for the Knoevenagel condensation of ethyl cyanoacetate and aromatic aldehydes along with the rate enhancement by microwave irradiation under solvent-free condition.

Knoevenagel condensation in the heterogeneous phase using KF-montmorillonite as a new catalyst

The Knoevenagel condensation of aromatic aldehydes was carried out in DMF as solvent on KF-Montmorillonite catalyst, using malononitrile and ethyl cyanoacetate as the acidic methylene reagents. Only the e isomers of the products were obtained and confirme

Microwave-assisted condensation reactions exploiting hexamethylenetetramine as a catalyst under solvent-free conditions

Hexamethylenetetramine has been exploited for the first time successfully as a catalyst for the Doebner reaction and Knoevenagel condensation along with the rate enhancement by microwave irradiation under solvent-free conditions.