2972-82-9

Usage

Uses

Used in Pharmaceutical Industry:
(BENZO[3,4-D]1,3-DIOXOLAN-5-YLMETHYLENE)METHANE-1,1-DICARBONITRILE is used as a key intermediate for the development of new drugs, leveraging its unique structural features to enhance the properties and effectiveness of pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical sector, (BENZO[3,4-D]1,3-DIOXOLAN-5-YLMETHYLENE)METHANE-1,1-DICARBONITRILE is utilized as a precursor in the synthesis of innovative pesticides, contributing to the creation of more efficient and targeted crop protection solutions.
Used in Organic Synthesis:
(BENZO[3,4-D]1,3-DIOXOLAN-5-YLMETHYLENE)METHANE-1,1-DICARBONITRILE is employed as a building block in the production of various heterocyclic compounds, which are essential in a wide array of applications, including medicinal chemistry and materials science, due to their diverse and valuable properties.

InChI:InChI=1/C11H6N2O2/c12-5-9(6-13)3-8-1-2-10-11(4-8)15-7-14-10/h1-4H,7H2

Upstream product

• 120-57-0 piperonal 
• 109-77-3 malononitrile 
• 4543-59-3 1,2-bis(3,4-dioxymethylenephenyl)ethane-1,2-diol 
• 89424-83-9 1,3-dihydroisobenzofuran-5-carbaldehyde 

Downstream Products

• 133405-30-8 2-Amino-4-benzo[1,3]dioxol-5-yl-6-thiophen-2-yl-isophthalonitrile 
• 134305-41-2 3-amino-4-cyano-5-(3,4-dioxymethylenephenyl)benzocoumarin 
• 133379-54-1 3-Amino-5-benzo[1,3]dioxol-5-yl-biphenyl-2,4-dicarbonitrile 
• 75076-20-9 (2S,5R)-4-Amino-2-benzo[1,3]dioxol-5-yl-5-(4-chloro-phenyl)-6-(ethyl-phenyl-amino)-2,5-dihydro-pyridine-3-carbonitrile 
• 75076-20-9 (2R,5R)-4-Amino-2-benzo[1,3]dioxol-5-yl-5-(4-chloro-phenyl)-6-(ethyl-phenyl-amino)-2,5-dihydro-pyridine-3-carbonitrile 
• 122135-17-5 4-Benzo[1,3]dioxol-5-yl-5-methyl-2-p-tolyl-2H-pyrazole-3-carbonitrile 
• 130715-43-4 3-amino-1-(benzo[d] [1,3]dioxol-5-yl)-1H-benzo[f]chromene-2-carbonitrile 
• 169267-80-5 ethyl 2-amino-3-cyano-6-methyl-4-(3,4-methylenedioxyphenyl)-4H-pyran-5-carboxylate 
• 259654-01-8 2,6-diamino-3,5-dicyano-4-(3,4-methylenedioxyphenyl)-4H-thiopyran 
• 463300-19-8 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile 
• 315246-09-4 2-amino-3-cyano-4-(4,3-methylenedioxyphenyl)-7-methyl-4H,5H-pyrano[3,2-c]pyran-5-one 

Relevant academic research and scientific papers

An Efficient Access to Pyrimidine-based Polyfunctional Heterocycles with Anticipated Antibacterial Activity

6-Amino-2-thioxotetrahydropyrimidine-5-carbonitrile derivative 2 was synthesized in a good yield via refluxing a mixture of arylidene 1 and thiourea in a highly basic sodium ethoxide solution. Subsequently, the synthesized pyrimidine-2-thione derivative 2 was allowed to interact with diversified nucleophiles and electrophiles under various reaction conditions in order to have a feasible access to further new and assorted fused heterocycles. Finally, the biological activity of the newly synthesized fused pyrimidines was screened in vitro against four different Gram-positive and Gram-negative bacterial strains. All the developed heterocycles were adequately characterized utilizing 1H-NMR, 13C-NMR, Fourier transform infrared, elemental analysis, and electrospray ionization–mass spectrum and tested for their antibacterial activity.

Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups

The first synthesis of 5,12-diamino-7,14-bis(aryl)-1,4,8,11-tetrathiacyclotetradeca-5,12-diene-6,13-dicarbonitriles was performed as a multicomponent macroheterocyclization of malononitrile, aryl aldehydes, and 1,2-ethanedithiol in the presence of a catal

Discovery of Highly Potent Adenosine A1Receptor Agonists: Targeting Positron Emission Tomography Probes

Adenosine receptor (AR) radiotracers for positron emission tomography (PET) have provided knowledge on the in vivo biodistribution of ARs in the central nervous system (CNS), which is of therapeutic interest for various neuropsychiatric disorders. Additio

Rapid and efficient uncatalyzed knoevenagel condensations from binary mixture of ethanol and water

This paper presents a new green protocol for Knoevenagel condensations of aldehydes and compounds with an active methylene group in a binary mixture of ethanol/water (3:7, v/v). This medium favored the uncatalyzed Knoevenagel reactions and easy workup pro

Contemporary development in sequential Knoevenagel, Michael addition multicomponent reaction for the synthesis of 4-Aryl-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile

An uncatalyzed efficient synthesis of bioactive pyridine derivatives has been investigated for the first time by a three-component sequential multicomponent reaction tackled with aromatic aldehydes, malononitrile, and 1,3-indandione via Knoevenagel condensation followed by Michael addition. The difference between the domino multicomponent and sequential multicomponent reaction is emphasized by this methodology. The reaction proceeds at ambient temperature without frequently useful N-source like ammonium salt for the construction of N-heterocycles, which makes this protocol a novel synthetic route for the preparation of the indenopyridine skeleton.

Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water

Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.

A new and efficient ZnCl2-catalyzed synthesis and biological evaluation of novel 2-amino-3,5-dicyano-4-aryl-6-aryl-aminopyridines as potent antibacterial agents against Helicobacter pylori (HP)

Here a new and efficient method via ZnCl2-catalyzed direct cyclization of diverse benzylidenemalononitriles and arylamines has been developed. With this method, a variety of novel 2-amino-3,5-dicyano-4-aryl-6-aryl-aminopyridines (2a-2v) could be easily prepared under the mild conditions with board substrate/functional group tolerance and decent product yields. The biological activities of the selected compounds (2c, 2e, 2g, 2i, 2k, 2m, 2n and 2o) has also been evaluated as new antibacterial agents. The results demonstrated that almost all of the compounds had more potent antibacterial activities against HP than that of clinically used drugs, Ornidazole, Metronidazole, Nitrimidazine and Clarithromycin, suggesting that further development of such compounds might be of great interest.

Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation

Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.

Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase

Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM).

On-column solvent-free oxidative cleavage reactions of vicinal diols by silica gel and paraperiodic acid: Application to in-situ sequential oxidation and Knoevenagel reactions

An on-column solvent-free oxidative cleavage reaction of vicinal diols by paraperiodic acid supported on silica gel at room temperature is described. The resulting pure carbonyl compounds are prepared in good to excellent yields with short reaction times. The cleavage reactions proceed under mild conditions, which avoids further cyclization reactions of the product dialdehydes. This method is also used for sequential oxidation and Knoevenagel reactions to prepare condensation products in good yields by using paraperiodic acid on a mixed bed of alumina and silica gel. The on-column solvent-free oxidative cleavage reaction of vicinal diols by paraperiodic acid supported on silica gel at room temperature is investigated. This approach is applied to an oxidation andKnoevenagel reaction sequence by using a mixed bed of alumina and silica gel to give condensation products in good yields. Copyright