S. V. Fedoseev

Domino-synthesis and fluorescence properties of 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles

Non-catalytic conversion of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the presence of water leads to the formation of a mixture of fluorescent 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles in equal proportions. This transformation was explained, spectral-luminescence properties were investigated, and fluorescence quantum yield was measured.

Spiro heterocyclization of 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles to 3H-pyrrole derivatives, 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes

Abstract4-Aryl-3-methyl-4-oxobutane-1,1,2,2-tetracarbonitriles reacted with morpholine to give 8-amino-3-aryl-1-imino-4-methyl-6-(morpholin-4-yl)-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles.

Interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with Lawesson's reagent – a new approach to the synthesis of 2,2′-disulfanediylbis(1H-pyrroles). The synthesis of photochromic diarylethene with a disulfide bridge

Transformation of 4-oxoalkane-1,1,2,2-tetracarbonitriles under the action of Lawessons reagent leads to 2,2′-disulfanediylbis(1H-pyrrole-3-carbonitriles) in good yields. The developed method allowed the synthesis of photochromic 2,2′-disulfanediylbis(4,5-bis(2,5-dimethylthiophen-3-yl)-1H-pyrrole-3-carbonitrile).

Directed synthesis of alkyl-substitued pyrrolo[3,4-c]pyrrole-1,3,4,6-tetraones

Reactions of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with aqueous hydrohalic acid led to the formation of alkyl-substituted pyrrolo[3,4-c]-pyrrole-1,3,4,6-tetraones.

Hydrolysis and acylation of imino group in E/Z-isomers of 3,4-dialkyl-8-amino-1-imino-6-morpholin-4-yl-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles

Acid-catalyzed hydrolysis of 3,4-dialkyl-substituted 8-amino-1-imino-6-morpholin-4-yl-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles under mild conditions led to the formation of 8-amino-6-morpholin-4-yl-1-oxo-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles, and their acylation afforded N-(8-amino-9-cyano-6-morpholin-4-yl-2-oxa-7-azaspiro-[4.4]nona-3,6,8-trien-1-ylidene)acetamides. The NMR spectra of compounds synthesized in contrast to the spectra of initial N-unsubstituted imins contained no doubled proton and carbon signals.

The rare transformation of 2,7-diazaspiro[4.4]nonanes in furo[3,4-c]pyridines

Transformation of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-en-4-carbonitriles in concentrated hydrohalic acid media leads to the obtaining of two classes of fused heterocycles: 4-halogen-3-hydroxy-1,3-dihydrofuro[3,4-c]pyridin-1-ones and octahydropyrrolo[3,4-c]pyrrole-1,3,4,6-tetraones.

New push–pull chromophores. Synthesis of 2-[4-Aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrol-2(5H)-ylidene]malononitriles

Abstract2-Aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer) reacted with 1-arylpropane-1,2-diones in ethanol in the presence of piperidine to give new donor–acceptor chromophores, 2-[4-aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrole-2(5H)-ylidene]malononitriles.

One-pot synthesis of 2-Oxo-1,2-dihydropyridine-3,4-dicarbonitriles

A pyridone fragment with a cyano group is present in compounds with a wide range of biologic activity: antiphlogistic [1], analgesic [1], anticancer [2, 3], and cardiotonic [4] action. It is also known that pyridin-2one contained in the composition of 2-oxo-1,2dihydropyridine-3,4-dicarbonitriles is a fluorophore [5–9]; it is stated in [5] that the presence of a cyano group increases the fluorescence quantum yield. Up till now a number of publications appeared describing the synthesis of various 2-oxo-1,2-dihydropyridine-3,4dicarbonitriles [10–14]. The simplest procedure for the preparation of these heterocycles is the synthesis from 4-oxoalkane-1,1,2,2-tetracarbonitriles with the help of diverse acids [10–12].

Synthesis of photochromic maleimides containing dithienylethene and azobenzene fragments

Maleimides containing dithienylethene and azobenzene fragments have been synthesized by reaction of dithienyl-substituted maleic anhydrides with 4-aminoazobenzene in boiling toluene in the presence of triethylamine, and their photosensitivity has been studied.

Rearrangement of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the directed synthesis of aryl-substituted 2-(3-cyano-5-hydroxy-1,5-dihydro-2 H -pyrrol-2-ylidene)malononitriles

3-Aryl-4-oxoalkane-1,1,2,2-tetracarbonitriles were synthesized by the interaction of 2-aryl ketones with tetracyanoethylene. Directed rearrangement of them in acetic acid in the presence of ammonium acetate led to the formation of 2-(3-cyano-5-hydroxy-1,5-dihydro-2Hpyrrol-2-ylidene)malononitriles containing an aryl substituent in conjugation with the acceptor buta-1,3-diene-1,1,3-tricarbonitrile moiety.