28752-91-2

Usage

Molecular structure

2-(dimethylaminomethylidene)indene-1,3-dione

Type of compound

Organic compound

Use

Reagent in organic synthesis

Characteristic features

Indene-1,3-dione core with a dimethylaminomethylidene substituent

Reactions

Ability to react with a variety of nucleophiles, such as alkoxides, amines, and enolates

Applications

Building block in the synthesis of pharmaceuticals and agrochemicals, formation of heterocyclic compounds (e.g. pyrazoles, pyrazines, and pyrroles), precursor in the synthesis of various materials (e.g. polymers, metal-organic frameworks)

InChI:InChI=1/C12H11NO2/c1-13(2)7-10-11(14)8-5-3-4-6-9(8)12(10)15/h3-7H,1-2H3

Upstream product

• 81054-40-2 1,3,4-Dioxathian-2,6-dispiro-bis<2'-(1,3-dioxo-indan)>-4,4-dioxid 
• 124-40-3 dimethyl amine 
• 81054-58-2 Kalium-(2-chlor-1,3-dioxo-indan-2-yl)-methansulfonat 
• 81066-47-9 (2-Chlor-1,3-dioxo-indan-2-yl)-methansulfonylchlorid 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 53162-69-9 2-(N'-phenylhydrazinomethylene)indane-1,3-dione 
• 496024-68-1 2-[(4-phenylpyrazol-3-ylamino)methylene]-1,3-indenedione 
• 658693-49-3 2-[(3-phenylpyrazol-5-ylamino)methylene]-1,3-indenedione 
• 81054-84-4 2-((2-(4-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 650597-81-2 1H-indeno[1,2-b]pyridine-2,5-dione 
• 1318754-02-7 2-[2-(1,3-diphenyl-1,3-dihydro-2H-benzimidazol-2-ylidene)ethylidene]-1H-indene-1,3(2H)-dione 
• 1224734-29-5 2-((2-(2-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-30-8 2-((2-(3-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-27-3 2-((2-p-tolylhydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-28-4 2-((2-(4-isopropylphenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 53162-10-0 1-phenylindeno<1,2-c>pyrazol-4(1H)-one 

Relevant academic research and scientific papers

Indenopyrazole oxime ethers: Synthesis and β1-adrenergic blocking activity

This paper reports the synthesis and cardiac activity of new β-blockers derived from (Z/E)-indeno[1,2-c]pyrazol-4(1H)-one oximes (5a,b). The latter compounds were allowed to react with epichlorohydrin, followed by reacting the oxiranyl derivatives formed

New access to indenopyridine, indenothiophene, indenoisoxazole, indenopyrazole, 2,2-bis (2,5-dihydroxyphenyl)indane-1,3-dione and indane-1-one derivatives

SEVERAL new indenopyridine, indenothiophene, indenoisoxazole, indenopyrazole, 2,2-bis (2,5-dihydroxyphenyl) indane-1,3-dione and indane-1-one derivatives which have a biological usage as potential biodegradable agrochemicals, and blood anticoagulants were prepared from cyclic ketones (1a-d) and active methylene nitriles (2a,b) as starting components.

Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors

Biological screening of (hetero)aromatic compounds allowed the identification of some novel inhibitors of Aβ1-40 aggregation, bearing indane and indole rings as common scaffolds. Molecular decoration of lead compounds led to inhibitors exhibiting a potency, measured by the Thioflavin T fluorimetric assay, ranging from high to low micromolar IC50. The 2-(p-isopropylphenyldiazenylmethylene)indolone derivative 6c resulted as the most potent aggregation inhibitor exhibiting an IC50 of 1.4?μM, with complete lack of fibril formation as confirmed by transmission electron microscopy. Structure-activity relationships suggested that binding to the Aβ peptide may be largely guided by π-stacking and hydrogen bond interactions.

Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives

A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5- phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC50 = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC50 = 124 nM) but highly selective PBR ligand.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. I. Synthesis of 1,5-Disubstituted 4-Acylpyrazoles

Reaction of open-chain and cyclic sym-1,3-diones with N,N-dimethylformamide dimethyl acetal gave, generally in high yield, a series of sym-2-dimethylaminomethylene-1,3-diones which reacted with phenylhydrazine and methylhydrazine to afford, generally in satisfactory yield, a number of 1,5-disubstituted 4-acylpyrazoles.The applications and limits of this new pyrazole synthesis are presented and discussed.