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The synthesis of thienocycloheptenoindoles
1984
A synthesis of the methylthieno[3,2-c]cyclohepteno[b]indole 7 from 2-methylthieno[3,2-b]cycloheptanone 3 is described. Unsuccessful attempts to prepare the isomeric thienocycloheptenoindole system present in formula 2, from the dihydrobenzothiophenone 8, and from derivatives of 5-(2-thienyl)-4-oxopentanoic acid, 17 and 18, and from N-benzylcycloheptindol-1-one 22 were unsuccessful. The preparation of 4,5-dihydro-2-phenyl-1-thienylmethyl-3H-pyridazin-3-one 20 and of the 5-aminopyrazole 21 are reported.
Comparison of spin density calculation methods for various alkyl-substituted 9,10-anthraquinone anion radicals in the solution phase
1996
EPR and ENDOR spectra were recorded for 2-methyl-9,10-anthraquinone (2-methylAQ), 2-ethylAQ, 2-tertbutylAQ and 2,3-dimethylAQ anion radicals in the solution phase. The EPR spectra were simulated with the help of ENDOR data. The experimental isotropic hyperfine coupling constants (IHFCs) were compared with calculated values from semi-empirical INDO, spin-restricted AM1/CI and B3PW91 density-functional methods. The best computational methods for the IHFCs were the semi-empirical AM1/CI method and the B3PW91 density-functional method with a large basis set.
1,4-Naphthoquinones as inducers of oxidative damage and stress signaling in HaCaT human keratinocytes.
2010
Selected biological effects of 1,4-naphthoquinone, menadione (2-methyl-1,4-naphthoquinone) and structurally related quinones from natural sources--the 5-hydroxy-naphthoquinones juglone, plumbagin and the 2-hydroxy-naphthoquinones lawsone and lapachol--were studied in human keratinocytes (HaCaT). 1,4-naphthoquinone and menadione as well as juglone and plumbagin were highly cytotoxic, strongly induced reactive oxygen species (ROS) formation and depleted cellular glutathione. Moreover, they induced oxidative DNA base damage and accumulation of DNA strand breaks, as demonstrated in an alkaline DNA unwinding assay. Neither lawsone nor lapachol (up to 100 microM) were active in any of these assay…
Cyclocondensation reaction of 1,2-diamino-4-methylbenzene andp-substituted acetophenones
1993
1,2-Diamino-4-methylbenzene 1 reacts in the presence of sulphuric acid with 4-substituted acetophenones 2a-e yielding 2,4-diaryl-2,3-dihydro-2,8-dimethyl-1H-1,5-benzodiazepines 3a-e and as minor component 2,4-diaryl-2,3-dihydro-2,7-dimethyl-1H-1,5-benzodiazepines 4a-e. The ratio 3:4 is in the range of 7:3. The structure determination of the regioisomers was performed by NOE measurements.
Electrochemical carboxylation of aldehydes and ketones with sacrificial aluminum anodes.
1986
Abstract The electrocarboxylation of aldehydes to the corresponding α-hydroxyacids was described as impossible with conventional electrochemical systems. It is reported here that it is possible to realize it in diaphragmless cells making of sacrificial aluminum anodes. The method can be used also for the electrocarboxylation of ketones with good yields.
Influence of the nature of the substrate and of operative parameters in the electrocarboxylation of halogenated acetophenones and benzophenones
2005
Abstract The electrocarboxylation of halogenated acetophenones and benzophenones to the corresponding hydroxycarboxylic acids has been carried out in undivided cell equipped with aluminium sacrificial anode and using 1-methyl-2-pyrrolidinone (NMP) as the solvent. The radical anion generated by the electro-reduction of the aromatic ketone is involved in several competitive reactions which lead to the formation of the target hydroxycarboxylic acid, the corresponding alcohol and pinacol and the de-halogenated parent ketone. If sufficiently negative working potentials are imposed, the latter is reduced to the corresponding carboxylate, pinacol and alcohol. Very different results in terms of sel…
Studien zum Vorgang der Wasserstoffübertragung, 73. Die Reduktion prochiraler Alkyl(aryl)ketone zu Carbinolen und Pinakolen mit Alkaliamalgamen
1984
Es werden die Faktoren ermittelt, welche die Stereochemie und das Mengenverhaltnis (C/P) des bei der Reduktion von Acetophenon mit Lithium-, Natrium- und Kaliumamalgam (Li/Hg, Na/Hg, K/Hg) gebildeten Carbinols (C) und Pinakols (P) bestimmen. Das C/P-Verhaltnis wird beeinflust a) durch Protonendonatoren, b) durch quartaren Ammoniumsalze, c) durch bis-tertiare Amine. Bei Anwesenheit von optisch aktiven quartaren Ammoniumsalzen und optisch aktiven bis-tertiaren Aminen wird sowohl beim Pinakol als auch beim Carbinol eine geringe optische Induktion beobachtet. Bei der Reduktion von Pivalophenon mit Li/Hg entsteht das anomale Dimerisierungsprodukt 20. Studies on the Occurrence of Hydrogen Transfe…
Synthèse de chalcones à base de tétrathiafulvalène: RC(O)CHC(CH3)TTF, TTFC(O)CHC(CH3)R (R TTF: C6H3S4; Bct: C6H5Cr(CO)3; Fc: C5H4FeC5H5). Propr…
1992
Abstract Novel chalcones that contain tetrathiafulvalene (TTF) and/or metallocene (ferrocenyl or benchrotrenyl) moieties: RC(O)CHC(CH 3 )R′ (R and/or R′ TTF: C 6 H 3 S 4 ; Fc: C 5 H 4 FeC 5 H 5 ; Bct: C 6 H 5 Cr(CO) 3 ) were prepared using TiCl 3 /Et 3 N as the condensation reagent. The 1-1 charge transfer complex with TCNQ (tetracyanoquinodimethane was obtained for the ditetrathiafulvalenic derivative (R R′ TTF). This complex exhibits the semiconducting behaviour.
Durability of a strach-based biodegradable polymer
2007
Abstract The photo-oxidation and the photo-stabilization of a commercial biodegradable polymer have been investigated in order to establish the possibility of using this polymer as raw material for films for agriculture. The degradation has been followed by measuring the mechanical properties as a function of photo-oxidation time and in particular by following the elongation at break. The virgin polymer, made from maize starch and a synthetic biodegradable polyester, shows poor resistance to the UV irradiation as observed by the fast decay of the elongation at break, but the presence of small amounts of conventional UV stabilizers strongly improves the durability of this polymer. The UV sta…
A new strategy for the synthesis of fluorinated 3,4-dihydropyrimidinones
2009
A new family of 3,4-dihydropyrimidinones (DHPMs) bearing fluorinated substituents at C6 have been prepared from gem-difluorinated nitriles, alkyl 3-butenoates and iso(thio)cyanates. This novel Biginelli-type process relies on the gamma-addition of the ester-derived enolate to fluorinated nitriles. A tandem nucleophilic addition aza-Michael reaction sequence completes the synthetic process. (C) 2009 Elsevier B.V. All rights reserved.