Synthesis of 4-Acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles

Russian Journal of Organic Chemistry - The reaction of 4-acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles with aromatic thiols in 1,4-dioxane in the presence of triethylamine led to the formation...     

Multicomponent synthesis of 2-alkylthio-6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocycloalkanes. Molecular and crystal structure of 6-amino-2-(2-methylbenzylthio)-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane

2-Alkylthio-6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocycloalkanes were synthesized via the reaction of cycloalkylidene malononitriles with cyanothioacetamide and alkyl halides. The structure of 6-amino-2-(2-methylbenzylthio)-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane was determined by the X-ray diffraction analysis.     

Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt

Russian Journal of General Chemistry - Condensation of benzaldehyde with malononitrile and malononitrile dimer (2-aminopropene-1,1,3-tricarbonitrile) in the presence of an excess of morpholine in...     

Studies on Antimicrobial Evaluation of Some 1-((1-(1H-Benzo[d]imidazol-2-yl)ethylidene)amino)-6-((arylidene)amino)-2-oxo-4-phenyl-1, 2-dihydropyridine-3,5-dicarbonitriles

A new series of 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((arylidene)amino)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles (4a–o) have been synthesized for the development of antimicrobial agents. Newly synthesized compounds were evaluated for their in vitro antibacterial activity against Gram-positive bacteria (Pseudomonas aeruginosa, Streptococcus pyogenes), Gram-negative bacteria (Escherichia coli, Staphylococcus aureus), and antifungal activity (Candida albicans, Aspergillus niger, Aspergillus clavatus). These compounds were characterized by infrared, ¹H NMR, ¹³C NMR, and mass spectra. The synthesized compounds 4b, 4e, 4 h, and 4k showed potent antimicrobial activity against tested microorganisms.     

Synthesis, Dimeric Crystal Structure, and Biological Activities of N- （ 4-Methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl ） -N＇- （ 2-trifluoromethyl-phenyl ） -guanidine

The title compound, N-（4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl）-N＇-（2-tritluoromethyl-phenyl）-guanidine, was synthesized and its structure was confirmed by using IR, MS,^1H NMR, and elemental analysis. The single crystal structure of the title compound was determined by X-ray diffraction. The preliminary biological test showed that the synthesized compound has a weak herbicidal activity.     

Structural, spectral and thermal studies of N-2-(4-picolyl)- and N-2-(6-picolyl)-N′-(2-chlorophenyl)thioureas and N-2-(6-picolyl)-N′-(2-bromophenyl)thiourea

N-2-(4-picolyl)-N′-2-chlorophenylthiourea, 4PicTu2Cl, monoclinic, P2₁/c, a=10.068(5), b=11.715(2), β=96.88(4)°, and Z=4; N-2-(6-picolyl)-N′-2-chlorophenylthiourea, 6PicTu2Cl, triclinic, P-1, a=7.4250(8), b=7.5690(16), c=12.664(3) Å, =105.706(17), β=103.181(13), γ=90.063(13)°, V=665.6(2) ų and Z=2 and N-2-(6-picolyl)-N′-2-bromophenylthiourea, 6PicTu2Br, triclinic, P-1, a=7.512(4), b=7.535(6), c=12.575(4) Å, a=103.14(3), β=105.67(3), γ=90.28(4)°, V=665.7(2) ų and Z=2. The intramolecular hydrogen bonding between N′H and the pyridine nitrogen and intermolecular hydrogen bonding involving the thione sulfur and the NH hydrogen, as well as the planarity of the molecules, are affected by the position of the methyl substituent on the pyridine ring. The enthalpies of fusion and melting points of these thioureas are also affected. ¹H NMR studies in CDCl₃ show the NH′ hydrogen resonance considerably downfield from other resonances in their spectra.     

Self-Catalyzed One-Pot Four-Component Green Synthesis of 2-Amino-6-[1,4-dioxo-3,4-dihydrophthalazin-2(1H)-yl]-4-phenyl-4H-pyran-3,5-dicarbonitriles

Russian Journal of Organic Chemistry - The title compounds were synthesized in good yields by one-pot four-component condensation of phthaloyl dichloride, ethyl cyanoacetohydrazide, malononitrile,...     

Copper(II) complex with 6-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidin-4-amine: synthesis,crystal structure,and electronic spectroscopy

A copper(II) complex with 6-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidin-4-amine (L), [CuLCl₂], has been synthesized. This compound is formed irrespective of the Cu?:?L molar ratio (Cu?:?L?=?1?:?1, 2?:?1, and 20?:?1) in the MeOH/H₂O/DMF mixture as a single product. ESI-MS data demonstrate that the additional amount of CuCl₂ above the Cu?:?L?=?1?:?1 molar ratio, is effectively solvated, and high-nuclearity species are formed in trace amounts in the solution. The complex adopts a distorted square-pyramidal geometry with two chlorides and three nitrogen atoms from L. The electronic spectrum of the complex contains a broad band with a maximum at 12,820?cm^?1 within the region characteristic for square-pyramidal chromophores CuA₅ (A?=?Cl, N). Due to Cu?···?Cl contacts, the molecules of [CuLCl₂] form the dinuclear [CuLCl₂]₂ unit. Surprisingly, the NH₂-group participates in the formation of NH?···?Cl hydrogen bonds instead of the formation of (NH?···?N3_(pyrimidine))₂ synthon, which is common for N-heteroaromatic compounds containing the NH₂-group in the α-position to aza-atom. These hydrogen bonds together with Cu?···?Cl contacts result in the formation of a 3-D-structure.     

Synthesis of Ethyl 5-(Arylcarbamoyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylates

Russian Journal of Organic Chemistry - A one-step procedure has been developed for the synthesis of previously unknown ethyl 5-(arylcarbamoyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylates by...     

Direct synthesis of 3,5-diaryl-1,2,4-oxadiazoles using 1-(2-oxo-2-arylethyl)pyridin-1-iums with benzamidines

An efficient domino protocol for the synthesis of 1,2,4-oxadiazole derivatives from readily available 1-(2-oxo-2-arylethyl)pyridin-1-iums and amidine hydrochlorides was developed. In this practical approach, N-acyl amidine precursors were formed firstly via a simple nucleophilic substitution, without the purification of N-acylamidine intermediates, and the following intramolecularly dehydrative cyclization gave 1,2,4-oxadiazole derivatives in the presence of I₂/K₂CO₃/DMSO, which exhibited excellent functional group tolerance and proceeded under simple experimental conditions.     

One-pot non-cyanide synthesis of 1-(pyridin-2-yl)isoquinoline-3-carbonitrile by reaction of 1-phenyl-2-[6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5-yl]ethanone with 1,2-dehydrobenzene in the presence of isoamyl nitrite

Russian Journal of Organic Chemistry - The reaction of 1-phenyl-2-[6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5-yl]ethanone with 1,2-dehydrobenzene generated in situ from anthranilic acid and excess...     

Synthesis and Reactions of 5-Amino-3-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-7-phenyl-7 H -thiazolo[3,2- a ]pyrimidine-6-carbonitrile

5-Amino-3-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-7-phenyl-7H-thiazolo[3,2-a]pyrimidine-6-carbonitrile was synthesized via the reaction of 4-(2-aminothiazol-4-yl)-3-methyl-1-phenyl-2-pyrazolin-5-one with benzylidene malononitrile and was then transformed to related fused heterocyclic systems. The antifungal and antibacterial studies revealed in some cases excellent biocidal properties.     

Reactions of 3-amino-1-phenyl- and 3-amino-1-(thien-2-yl)-4,4,4-trifluorobut-2-en-1-ones with 1,2-diaminopropane and 1,2-diamino-3,3,3-trifluoropropane

The reactions of 3-amino-1-phenyl-and 3-amino-1-(thien-2-yl)-4,4,4-trifluorobut-2-en-1-ones with 1,2-diaminopropane under kinetically controlled conditions afford mixtures ofcis andtrans isomers of 2-aroylmethyl-4-methyl-2-trifluoromethylimidazolidines. Analogous reactions with 1,2-diamino-3,3,3-trifluoropropane yieldcis-2-aroylmethyl-2,4-bis(trifluoro-methyl)imidazolidines. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2135–2139, November, 1999.     

Preparation of (2E,6E)-10,11-dihydrofarnesol via a (bisphenyl)dithioacetal reduction

Reduction of a (bisphenyl)dithioacetal with sodium/isopropyl alcohol in THF allows preparation of (2E,6E)-10,11 -dihydrofarnesol in high yield.     

Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3-phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one

Three procedures were used for the synthesis of -, , and -pyridyl-substituted (5Z)-3-phenyl-5-(pyridylmethylene)-2-thiohydantoins: the reaction of 2-thiohydantoin with the corresponding aldehyde in AcOH in the presence of AcONa, the two-step one-pot synthesis with the use of the same starting compounds, and three-component condensation of aryl isothiocyanate, glycine, and aldehyde in AcOH. Alkylation of the resulting thiohydantoins with iodomethane in the presence of a base afforded the corresponding S-methylated derivatives, viz., 2-methylthio-3-phenyl-5-(pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones. The structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thioxoimidazolin-4-one and (5Z)-2-methylthio-3-phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one were established by X-ray diffraction analysis.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2734–2739, December, 2004.