16954-74-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 18, p. 1813, 1977 DOI: 10.1016/S0040-4039(01)83612-1

InChI:InChI=1/C12H4N2O2/c13-5-7(6-14)10-11(15)8-3-1-2-4-9(8)12(10)16/h1-4H

Upstream product

• 203795-20-4 1′,3′-dioxo-1′,3′-dihydrospiro[cyclopropane-1,2′-indene]-2,2,3,3-tetracarbonitrile 
• 938-24-9 indantrione 
• 109-77-3 malononitrile 
• 485-47-2 indan-1,2,3-trione hydrate 

Downstream Products

• 117457-21-3 (1,3-Dioxo-indan-2-ylidene)-[(pyridin-2-ylmethyl)-amino]-acetonitrile 
• 136829-54-4 ethyl 4,4-dicyano-2,2,4,5-tetrahydro-5-oxo-2,2,2-triphenyl-indeno<2,1-e>-1,3,2-oxazaphosphorine-(2H)-carboxylate 
• 136829-53-3 2,2,2,3-tetrahydro-5-oxo-2,2,2,3,3-pentaphenylindeno<2,1-e>-1,2-oxaphosphorin-4,4(5H)-dicarbonitrile 
• 117457-12-2 {[Cyano-(1,3-dioxo-indan-2-ylidene)-methyl]-amino}-acetic acid ethyl ester 
• 57133-84-3 C₁₉H₁₈P⁽¹⁺⁾*C₁₂H₄N₂O₂^(1-) 
• 117457-15-5 {[Cyano-(1,3-dioxo-indan-2-ylidene)-methyl]-amino}-phenyl-acetic acid methyl ester 
• 136829-46-4 2,3-dihydro-5-oxo-2-thio-3-(triphenylphosphoranylidene)indeno<1,2-b>pyran-4,4(5H)-dicarbonitrile 
• 130670-81-4 2-Amino-3-(4-nitro-phenylazo)-9-oxo-9H-1,4,10a-triaza-cyclopenta[b]fluorene-10-carbonitrile 
• 136829-45-3 (4,4-dicyano-4,5-dihydro-2-hydroxy-5-oxoindeno<1,2-b> pyran-3-yl) triphenylphosphonium hydroxide inner salt 
• 136829-51-1 α--3-hydroxy-1-oxo-indene-2-propionate 
• 136829-50-0 methyl-β,β-dicyano-3-hydroxy-1-oxo-α-(triphenylphosphoranylidene)indene-2-propionate 
• 127207-62-9 <1,3-Dioxo-2-indanyl><4-(1,4,7,10-tetraoxa-13-aza-13-cyclopentadecyl)phenyl>malononitril 
• 136829-52-2 3-hydroxy-1-oxo-α-<α-(triphenylphosphoranylidene)phenacyl>indene-2-malononitrile 
• 117457-10-0 {[Cyano-(1,3-dioxo-indan-2-ylidene)-methyl]-amino}-acetic acid 

Relevant academic research and scientific papers

One-pot of three-component synthesis of novel amino-spiroindene derivatives

A facile and efficient one-pot three-component synthesis of the amino-spiroindene derivatives was achieved, via the reaction of ninhydrin, malononitrile or ethylcyanoacetate and various reagents including 1, 2- and 1,3-dicarbonyl compounds/enols. Graphical Abstract: [Figure not available: see fulltext.].

REACTION OF 2-DICYANOMETHYLENEINDAN-1,3-DIONE WITH PYRROLES AND INDOLES

The reaction of 2-dicyanomethyleneindan-1,3-dione with pyrrole, indole, and their methyl derivatives gives products of addition at the dicyanomethylene carbon atom, viz., pyrrolyl- and indolyl(1,3-dioxo-2-indanyl)malononitriles, which upon heating or irradiation with UV light irreversibly split out HCN to give deeply colored products of replacement of the nitrile group in the acceptor by a heterocyclic grouping.Data from the UV and PMR spectra of the compounds obtained are presented.

Introducing new method for the synthesis of polycyclic compounds containing [1,3]dithiine derivatives, with anticancer and antibacterial activities against common bacterial strains between aquatic and human

In this study, glycerol:potassium carbonate used as a green deep eutectic solvent, for synthesis of polycyclic compounds containing [1,3]dithiine derivatives. The antimicrobial properties of the derivatives against Lactococcus garvieae and Edwardsiella tarda were tested as bacterial strains between aquatic and human based on the minimum inhibitory concentration (MIC), the minimum lethal concentration (MBC) and inhibition zone diameter (IZD). In addition to antimicrobial properties, cytotoxicity testing was performed against MCF-7 breast cancer cells via MTT cell viability assay.

Amine-promoted one-pot, Multicomponent route to spiro-fused-pyran derivatives in aqueous media

The primary amine-promoted synthesis of spiro-fused-pyran derivatives via the three-component reaction of ninhydrin, malononitrile, and cyclic 1,3-diketo compounds is described. This new methodology affords the title compounds in high yields and short time, and with easy workup without chromatographic purification steps or extraction. All structures were confirmed by IR, 1H- and 13C-NMR spectroscopy, and mass spectroscopy. A plausible mechanism for this type of reaction is proposed (Scheme 2). Copyright

Synthesis of heterocyclic [3.3.3]propellanes via a sequential four-component reaction

A highly chemoselective heteroannulation protocol for the synthesis of unreported polysubstituted heterocyclic [3.3.3]propellanes has been developed by sequential four-component reaction of ninhydrin, malononitrile, primary amines, and dialkyl acetylenedicarboxylates under mild conditions in water. To the best of our knowledge, there are no previous reports for the synthesis of these classes of heterocyclic [3.3.3]propellanes. The merit of this sequential Knoevenagel condensation/enamine formation/Michael addition/cyclization sequence is highlighted by its high atom-economy, excellent yields, the use of water as reaction media, and the efficiency of production without the use of any activator or metal promoters. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products were obtained simply by washing the crude products with 95% ethanol.

Facile one pot microwave assisted solvent-free synthesis of novel spiro-fused pyran derivatives via the three-component condensation of ninhydrin with malononitrile and active methylene compounds

Three-component condensation of ninhydrin, malononitrile, and some nucleophilic reagents in the presence of piperidine under microwave irradiation without solvent afforded the corresponding spiro-fused pyran derivatives. The structures of the products were proved by elemental analyses, IR, 1H NMR and MS spectroscopy.

Diverse structural assemblies of a series of ninhydrin derivatives: Quantitative analyses from experimental and theoretical studies

Three ninhydrin derivatives (2–4) have been synthesized where the reaction of ninhydrin with Meldrum's acid yielded [3.3.3] propellanoid (2) and ethyl 2,2-bis (1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetate (3) while with malononitrile yielded a spiroindenopyran (4). The products being crystalline in nature and are characterized by single crystal X-ray diffraction in addition to other spectroscopic studies. X-ray crystallography reveals that solid-state structure of the title compounds exhibits C?H···π, π?π and lone-pair(l.p)···π interactions in building supramolecular assemblies. Indeed, compound (2) was stabilized through extended supramolecular C?H···π/π?π/π···H?C network whereas compounds (3) and (4) are stabilized through lone-pair (l.p)···π and π?π interaction respectively. The diverse intermolecular interactions via Hirshfeld surface analysis enables quantitative contributions to the crystal packing that exposes the similarities and differences in the interactions experienced by each compound. The distinctive energy frameworks have been calculated for individual molecules and the interaction energies suggest that the contacts are largely dispersive in nature. The binding energies associated with the non-covalent interactions observed in the crystal structures have been calculated using theoretical DFT calculations. Finally, the interplay between the interactions have been characterized by Bader's theory of “atoms-in-molecules” (AIM).

Synthesis, characterization and antimicrobial evaluation of novel 6'-amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5'-carbonitrile derivatives

l,3-Dithiin with two sulfurs in its structure is a six-membered, sulfur-containing heterocyclic compound. New derivatives of 6'-amino-2'-(arylidene)spiro[indeno[1,2-b]quinoxaline[1,3]dithiine]-5'-carbonitrile were prepared by the multi-component reaction of active methylene compounds, carbon disulfide, malononitrile and multi-ring compounds containing a carbonyl group in the presence of piperidine as a catalyst at room temperature with high efficiency. The antimicrobial effects including antibacterial and antifungal effects based on inhibition zone diameter (IZD), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were studied.

Dihydro-2: H -thiopyran-3(4 H)-one-1,1-dioxide-a versatile building block for the synthesis of new thiopyran-based heterocyclic systems

Three series of new cyclic sulfones have been prepared by a one-pot multi-component reaction (MCR) starting from the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The in silico screening of the synthesized compounds revealed their high anti-inflammatory, antiarthritic, antiasthmatic and antiallergic potential coupled with the strong probability levels of cystinyl aminopeptidase inhibition. The key structures were confirmed by 2D NMR techniques.

Synthesis method of 1,4-dyhydroxyl-2,3-naphthyldinitrile and derivative thereof

The invention discloses a synthesis method of 1,4-dyhydroxyl-2,3-naphthyldinitrile and a derivative thereof. The method takes ninhydrin and a derivative thereof as raw materials, and the ninhydrin and the derivative thereof react with malononitrile in water to generate 2-(dicyanomethylene)indene-1,3-diketone and a derivative thereof; the 2-(dicyanomethylene)indene-1,3-diketone and the derivative thereof further react with anhydrous potassium iodide and are isomerized to generate potassium salt of the 1,4-dyhydroxyl-2,3-naphthyldinitrile; and after the potassium salt of the 1,4-dyhydroxyl-2,3-naphthyldinitrile is acidified and then is separated, the high-purity product (the 1,4-dyhydroxyl-2,3-naphthyldinitrile) is obtained. The method disclosed by the invention has the advantages of wide raw material resource and low price; the cost is low and the method is green and environmentally friendly; and the method is convenient for industrialized large-scale production.