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A highly diastereoselective method for the synthesis of novel spiro-tetrahydroquinoline derivatives is reported here, using a one-pot reaction method. All compounds were characterized by 1H-nuclear magnetic resonance (NMR) and mass spectroscopy, and their stereo configurations were confirmed by X-ray analysis. These activities of these derivatives were then tested in human keratocyte cells. The responses of cells to treatment with selected compounds were studied using scratch analysis, and the compounds were tested in a mouse excision wound model. Three of the derivatives demonstrated significant wound-healing activities.

Indandione is an important starting material that has drawn great attention in various organic transformations because of its attributes, such as low cost, easy to handle and eco-friendliness generally affording the corresponding products in excellent yields. In this review, we summarize recent data describing the most important MCRs reactions in which one of the starting materials is indandione. This review will also present two-, three-, four-, and five-component and one-pot reactions for the functionalization of indandione with the to increase awareness on the versatility of using this compound among organic chemists.

Cu doped ZnO nanocrystalline powder (10 mol%) has been found to be an efficient catalyst for the one-pot multi-component synthesis of fully substituted new indeno[1,2-b]pyridines through a combination of 1,3-indandione, propiophenone or acetophenone derivatives, aromatic aldehydes, and ammonium acetate in ethanol/H2O at room temperature. The methodology is mild, efficient and high to excellent yielding.

Indandione is an important starting material that has drawn great attention in various organic transformations because of its attributes, such as low cost, easy to handle and eco-friendliness generally affording the corresponding products in excellent yields. In this review, we summarize recent data describing the most important MCRs reactions in which one of the starting materials is indandione. This review will also present two-, three-, four-, and five-component and one-pot reactions for the functionalization of indandione with the to increase awareness on the versatility of using this compound among organic chemists.

Palladium-catalyzed asymmetric [3+2] cycloaddition of 3-diazooxindoles with 2-vinylspiro[cyclopropane-1,2′-indene]-1′,3′-dione proceeded smoothly in the presence of chiral imidazoline–phosphine ligands to give the corresponding highly functionalized spiropyrazolidine derivatives in good to excellent yields (52–99%) along with good enantioselectivities (48–82% ee) under mild conditions.

Efficient carbon–carbon bond-forming reaction at the 5- and 6-positions of catechol skeleton was achieved through anodic oxidation of catechol, 3-methylcatechol, and 4-methylcatechol in the presenc...

2-[(Trimethylsilylmethylamino)(methylthio)]methylene- and 2-[(trimethylsilylmethylthio)(methylthio)]methylene-1, 3-indandiones (1a, b), which are readily prepared by reaction of the corresponding 2-bis(methylthio)methylene-1, 3-indandione (12) with trimethylsilylmethylamine (13a) and trimethylsilylmethylmercaptan (13b), were found to be synthetic equivalents of carbonyl alkylidene-azomethine and alkylidene-thiocarbonyl ylides. Reaction of 1a, b with reactive hetero-dipolarophiles such as aldehydes and ketones and reactive alkenes in the presence of cesium fluoride gave 1, 3-dipolar cycloadducts, 4, 5-dihydro-2-(1, 3-dioxoindan-2-ylidene)-1, 3-oxazoles (6a-f, 7a-c), 4, 5-dihydro-2-(1, 3-dioxoindan-2-ylidene)pyrroles (8a-c), 2-alkylidene-1, 3-oxathiolanes (9a-k, 10a, b), and 2-alkylidenethiophenes (11a-c), via formation of the counterpart of the carbonyl-substituted intermediate with concomitant desilylation.

1,1-Dicyanomethylene-3-indanone (2) reacted with cinnamonitriles 1a-c to afford fluorenone derivatives 6a-c. Compounds 6a-c were also obtained when treating 2 with 1d-f. The coupling of 2 with aromatic diazonium chlorides resulted in the formation of the hydrazones 8a-c. 8a readily cyclized to indeno[2,1-c]pyridazine (9a) in acidic medium. The action of 1d-f on enaminone 3 was also studied.

Dibenzoylmethane dibromide (5) and 1,3-indandione dibromide (6) react with ylide-phosphoranes 1a[sbnd]c to give the α,β-unsaturated esters 10 and 13, respectively. All intermediates are isolated and identified. Structures 10 and 13 as well as the intermediates were confirmed by compatible analytical and spectroscopic results.

Conformational analysis in solution of 2-diphenylacetyl-1,3-indandione-1-hydrazone (DI- PAIN, 1) and its derivatives was achieved by NMR, FT-IR and fluorescence spectroscopy. The spectral evidence indicates that the enamine tautomer is the only isomeric form adopted in solution.

2-[(Trimethylsilylmethylamino)(methylthio)]methylene- and 2-[(trimethylsilylmethylthio)(methylthio)]methylene-1, 3-indandiones (1a, b), which are readily prepared by reaction of the corresponding 2-bis(methylthio)methylene-1, 3-indandione (12) with trimethylsilylmethylamine (13a) and trimethylsilylmethylmercaptan (13b), were found to be synthetic equivalents of carbonyl alkylidene-azomethine and alkylidene-thiocarbonyl ylides. Reaction of 1a, b with reactive hetero-dipolarophiles such as aldehydes and ketones and reactive alkenes in the presence of cesium fluoride gave 1, 3-dipolar cycloadducts, 4, 5-dihydro-2-(1, 3-dioxoindan-2-ylidene)-1, 3-oxazoles (6a-f, 7a-c), 4, 5-dihydro-2-(1, 3-dioxoindan-2-ylidene)pyrroles (8a-c), 2-alkylidene-1, 3-oxathiolanes (9a-k, 10a, b), and 2-alkylidenethiophenes (11a-c), via formation of the counterpart of the carbonyl-substituted intermediate with concomitant desilylation.

1-Benzyl-1, 4-dihydronicotinamide (1) and KCN reacted with 2-(o-bromomethyl)-benzylidene-1, 3-indandione (2) to give 7, 12-dihydro-1-oxoindeno[3, 2-c][2]benzooxepine (3) and 1′-cyano-3′-hydro-2, 2′-spirobi[2H-indene]-1, 3-dione (4), respectively, and the selectivity of O-alkylation and C-alkylation is discussed.

Aldehydes, 1,3-indandione and cyclohexylisocyanide undergo smooth coupling-cyclization in water to produce the corresponding 2-(cyclohexylamino)-3-aryl- indeno [1,2-b] furan-4-ones in good yields. Water was used as a solvent to avoid the use of other highly toxic and environmentally unfavorable solvents for this synthesis.

This is an environmentally friendly method in the field of electroorganic reactions under controlled potential electrolysis, without toxic reagents at a carbon electrode in an undivided cell which involves the (EC) mechanism reaction and comprises two steps alternatively; (i) electrochemical oxidation and (ii) chemical reaction. In particular, the electrochemical oxidation of 4-tert-butylcatechol, 4-methylcatechol and 2,3-dihydroxybenzoic acid in the presence of 2-phenyl-1,3-indandione has been studied in a water-acetonitrile (90 : 10) mixture. The research includes the use of a variety of experimental techniques, such as cyclic voltammetry, controlled-potential electrolysis, and spectroscopic identification of products (FT-IR, (1)H-NMR, and MS spectrometry).

Efficient syntheses, X-ray structures and spectroscopic properties of s-indacene-1,3,5,7(2H,6H)-tetraone (1) and 1,3-dioxo-5,6-indanedicarboxylic acid (2), their precursors and derivatives, are described for the first time.

The title compound, C20H19NO2, belongs to the class of donor–acceptor substituted conjugated polyenes. Within the structure, O atoms are situated in the plane of the 1,3-indandione fragment and the N atom lies in the plane of the p-benzylidene fragment, which forms a dihedral angle of 7.6 (2)° with the indandione nucleus.

In the title compound, 2-(4-chlorophenylhydrazono)-1,3-indandione (C 15 H 9 ClN 2 O 2 ), the indandione and phenylazo groups are connected by a C=N bond of 1.307 (3)A. The molecule is planar and the bond lengths correspond to those expected for a phenylhydrazone. A strong intramolecular N-H...O hydrogen bond was found.

In the title compound, C 17 H 14 N 2 O 2 , the 2-methyl-1,3-dioxoindan-2-yl and 2-methylphenyl groups are trans with respect to each other. The phenyl ring and the azo group are not coplanar and have a dihedral angle of 15,4 (2)° between their respective planes. Both benzene ring planes are almost planar within experimental error and the five-membered ring adopts an envelope conformation

The 2-methyl-1,3-indandione and 4-nitrophenyl groups are trans to each other. The five-membered ring of the indandione moiety adopts an envelope conformation. The phenyl and azo groups are not coplanar because of steric hindrance between the lone-pair orbitals at the carbonyl O and beta-N atoms [Cl'-N = N = 112.6 (6) and 112.8 (6)-degrees for molecules A and B, respectively].

In the title compound, C16H11ClN2O2, the 2-methyl-1,3-dioxoindan-2-yl and 4-chlorophenyl groups are trans to each other. The five-membered ring of the indandione moiety adopts an envelope conformation. The phenyl and azo groups are not coplanar because of steric hindrance between the lone-pair orbitals on the carbonyl O atom and beta-N atom [C-N=N = 112.4 (3)-degrees].

Attempted Mannich reaction with the title compound 1 using morpholine and formalin led to 2 or 4 according to the reaction conditions. Whereas, on using primary amines the diindeno [1,2-b:2',1'-e] pyridine (9-11) were obtained, in addition to 2-methylene-1,3-indandione (6), in case of 10 and 11. However, the Mannich bases 13-15 were formed on treating 2-benzylidene-1,3-indandione with the appropriate secondary amine. The structures 2, 9-11 were confirmed via unambiguous syntheses

Mannich reaction of 1,3-indandione-1-phenylhydrazone (1) or 1,3-diphenylhydrazone(5) with morpholine or piperazine gave the Mannich base-phenylhydrazone 2 and 3 or the diphenylhydrazone 6 and 7, respectively. Whereas, such reaction with 1 or 5 using primary amines afforded the indeno [2,1-f]-1,2,4-triazepin-6(2H)-one (4) or its 6-phenylhydrazone (8), respectively. Treatment of 5 with ammonium acetate and formalin afforded 9. The indeno [1,2-f]-1,2,4,5-tetrazepin-10(2H)-one (11) was obtained from the 1,2-diphenylhydrazone 10 and formaldehyde

Solvent Yellow 33 and a Solvent Green 3 mixture (30:70 mixture of Solvent Yellow 33 and Solvent Green 3) were not acutely toxic to seven of nine freshwater species when tested at the solubility limits of the dyes in freshwater. A solubility limit solution of the Solvent Green 3 mixture killed 50% of the rainbow trout tested for 96 h but was non-toxic when diluted by 50%. Both dyes caused a reduction in green algal growth at solubility limits. The Solvent Green 3 mixture was the most detrimental causing a 98–99% reduction in growth after 5 days of exposure.