Adduct of dimedone and 1,2-dibenzoylethene in reactions with nitrogen binucleophiles

Dimedone adduct with 1,2-dibenzoylethene in reaction with p-phenylenediamine formed a bispyrrole derivative, and with benzidine and ethylenediamine afforded the corresponding monopyrroles. The reaction of the initial adduct with tryptamine results in a product containing a pyrrole and an indole fragments. Both versions of N-heterocyclization proceed in the reaction with urea yielding derivatives of tetrahydroindole and pyrrole. In the reaction with hydrazine hydrate a substituted pyridazine was obtained as a result of a dimedone molecule elimination from the intermediate cyclization product.     

Syntheses of the marine alkaloids 6-oxofascaplysin,fascaplysin and their derivatives

A simple approach towards the pyrido[1,2-a:3,4-b′]diindole system via the reaction of indigo with methylene active compounds was used for the syntheses of the marine alkaloids 6-oxofascaplysin, fascaplysin, and their derivatives. It was also demonstrated that the reaction with ketones led to indigo decomposition and the formation of isatin derivatives. The derivative of fascaplysin with a phenyl substituent at C-7 demonstrated 2–3 times greater inhibitory activity against selected cancer cell lines than fascaplysin.     

Nitrogen-containing heterocycles derived from tetracarbonyl compounds and their analogs. Synthesis of 2-(4,4-dimethyl-2,6-dioxocyclohexyl)-1,4-diphenylbutane-1,4-dione and its reaction with N-nucleophiles

Condensation of dimedone with 1,2-dibenzoylethylene in the presence of base gave 2-(4,4-dimethyl-2,6-dioxocyclohexyl)-1,4-diphenylbutane-1,4-dione. Its reaction with amines gives the corresponding pyrrole derivatives.Far Eastern State University, Vladivistok 690600, Russia, Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1497–1499, November, 1999.     

Three-Component Condensation of Cyclic Enamino Ketones with Phenylglyoxal Hydrate and Ethyl Acetoacetate

Russian Journal of Organic Chemistry - Three-component condensation of cyclic enamino ketones with phenylglyoxal hydrate and ethyl acetoacetate in aqueous ethanol afforded a series of...     

Hydrolytic Degradation of Some Fused and Spiro Compounds Containing a System of 2-Amino-3-Cyano-4H-Pyran

Russian Journal of Organic Chemistry - Heating some derivatives of 5,6,7,8-tetrahydro-4Н-chromene and 1,2,5′,6′,7′,8′-hexahydrospiro-[indole-3,4′-chromene] in...     

Condensation Reactions of Sulfur-Containing Chalcone Analogs

Three-component condensation of heterocyclic chalcone analogs containing a thiophene ring with 5,5-dimethylcyclohexane-1,3-dione (dimedone) and ammonia at 140–145°C under pressure afforded functionalized 1,4,5,6,7,8-hexahydroquinoline derivatives; the corresponding triketones were formed under milder conditions (100–105°C). The condensation of 1,3-di(thiophen-2-yl)prop-2-en-1-one with dimedone and ammonia under harsh conditions unexpectedly produced functional 1,2,3,4,5,6,7,8,9,10-decahydroacridine derivative. Heterocyclic chalcone analogs reacted with ethyl acetoacetate in the presence of ammonia to give cyclocondensation products, ethyl 2-oxocyclohex-3-ene-1-carboxylates.     

Recyclization of dimedone adduct with 2-(2-oxo-2-phenylethylidene)propanedinitrile in the reaction with N-nucleophiles

Three-component condensation of dimedone with phenylglyoxal hydrate and malononitrile gave a polyfunctional 5,6,7,8-tetrahydro-4H-chromene derivative, 2-amino-4-benzoyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, which reacted with ammonium acetate to produce pyrrolo[3,4-c]quinoline ring system. Reactions of the condensation product with primary and secondary amines and hydroxylamine hydrochloride afforded polysubstituted pyrroles, whereas the reaction with hydrazine hydrate led to 3-amino-6-phenylpyridazine-4-carbonitrile.     

Reactions of dimedone-β-benzoylacrylic acid adduct with nitrogen-containing binucleophiles

2-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-4-oxo-4-phenylbutanoic acid (dimedone adduct with β-benzoylacrylic acid) reacted with ethylenediamine and benzidine to give bis-quinoline derivatives. In the reaction with tryptamine a product containing hexahydroquinoline and indole fragments was obtained, while the reaction with phenylhydrazine hydrochloride afforded pyridazine derivative. The reactions with o- and p-phenylenediamines involved retro-Michael decomposition of the initial adduct and formation of enamino derivatives of dimedone.     

Synthesis and spectral-luminescent properties of 5-substituted polyaryl derivatives of barbituric acid

New substituted barbituric acid derivatives containing a 4,5,6,7-tetrahydroindole moiety have been synthesized by three-component condensation. Luminescence of crystals and solutions of the compounds synthesized have been studied; a maximum luminescence intensity and a minimum Stokes shift have been found in the 1-naphthyl derivative.