52693-86-4

Usage

Uses

Used in Organic Synthesis:
(E)-1-(3,4-diMethoxybenzylidene)hydrazine is used as a synthetic building block for the preparation of various heterocycles and pharmaceuticals. Its unique structure allows for the creation of a wide range of complex molecules with potential applications in the medical and chemical industries.
Used in Coordination Chemistry:
In the field of coordination chemistry, (E)-1-(3,4-diMethoxybenzylidene)hydrazine serves as a chelating agent for transition metal ions. Its ability to form stable complexes with these metal ions makes it a valuable tool in the study and development of new materials and catalysts.
Used in Medicinal Chemistry Research:
(E)-1-(3,4-diMethoxybenzylidene)hydrazine has demonstrated potential biological activity, including antifungal and antiproliferative properties. This makes it a subject of interest for researchers in medicinal chemistry, who are exploring its potential as a therapeutic agent for various diseases and conditions.
Used in Antifungal Applications:
(E)-1-(3,4-diMethoxybenzylidene)hydrazine is used as an antifungal agent, exhibiting activity against various fungal pathogens. Its ability to inhibit fungal growth makes it a promising candidate for the development of new antifungal drugs and treatments.
Used in Antiproliferative Applications:
Due to its antiproliferative properties, (E)-1-(3,4-diMethoxybenzylidene)hydrazine is used in the development of compounds that can inhibit the proliferation of cancer cells. This application has significant potential in the field of oncology, as it may lead to the discovery of new cancer treatments and therapies.

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 5346-37-2 3,4-Dimethoxybenzaldehyde semicarbazone 

Downstream Products

• 40092-07-7 C₁₄H₂₁N₃O₃ 
• 17745-86-7 3,4-dimethoxybenzaldehyde N-[-(3,4-dimethoxyphenyl)methylidene] hydrazone 
• 1418317-22-2 (E)-1,2-dimethoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 40092-40-8 C₁₃H₁₉N₃O₃ 

Relevant academic research and scientific papers

Palladium-catalyzed hydroalkylation of methylenecyclopropanes with simple hydrazones

A palladium-catalyzed hydroalkylation reaction of methylenecyclopropanes via highly selective C-C σ-bond scission was achieved under mild conditions, in which simple hydrazones served as carbanion equivalents. This method featured good functional group compatibility, affording high yields of C-alkylated terminal alkenes.

Nickel-catalyzed cross-coupling of umpolung carbonyls and alkyl halides

An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides

An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Metal-Free Construction of the C(sp3)-CF3 Bond: Trifluoromethylation of Hydrazones with Togni's Reagent under Mild Conditions

A metal-free trifluoromethylation of hydrazones with Togni's reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)-CF3 bonds.

Umpolung cross-coupling of polyfluoroarenes with hydrazones: Via activation of C-F bonds

An umpolung strategy for the cross-coupling of polyfluoroarenes with various substituted hydrazones to construct C(sp2)-C(sp3) bonds is developed. In this strategy, the C-F bond of polyfluoroarenes is cleaved and coupled with moisture- and air-stable hydrazones under mild conditions with good to excellent yields. This method provides a useful tool for synthesizing polyfluorinated pharmaceuticals and functional materials.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)

A practical and convenient synthesis of (E)-β-(trifluoromethyl)styrenes has been achieved by the reaction of commercially available halothane (HCFC-123B1) and hydrazones prepared in advance in situ, in the presence of 1,2-ethylenediamine and a catalytic amount of CuCl2·2H2O at room temperature. The products showed acceptable to high yields and high to excellent stereoselectivity. This handy synthetic method provided easy access to a variety of (E)-β-(trifluoromethyl)styrenes.

A novel one pot multi-component strategy for facile synthesis of 5-aryl-[1,2,4]triazolidine-3-thiones

We have disclosed an efficient, one pot, novel multi-component approach for the synthesis of 5-aryl-[1,2,4]triazolidine-3-thiones from aldehyde, hydrazine hydrate, and trimethylsilyl isothiocyanate (TMSNCS) in the presence of catalytic amount of sulfamic acid. High yields, easy work-up procedure, no chromatographic separation, and novelty in multi-component strategy are the main merits of the present strategy.

Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)

In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase. Taylor &Francis Group, LLC.

Synthesis and Diels-Alder reactions of α-fluoro- and α-trifluoromethylacrylonitriles

A novel synthetic method for the preparation of α-fluoro- and the still unknown α-trifluoromethylacrylonitriles is elaborated. The reaction of α-fluorovinylbromides and α-trifluoromethylvinylbromides with CuCN leads to the title compounds in good to high yields. While the α-fluoroacrylonitriles were isolated as mixture of Z/E-isomers, the α-trifluoromethylacrylonitriles were obtained as pure Z-isomers. The α-trifluoromethylacrylonitriles are shown to be excellent dienophiles for Diels-Alder reactions.