Alkylation reactions of 5-nitrofurfuryl derivatives as C-acids

1979 ◽  
Vol 44 (8) ◽  
pp. 2511-2516 ◽  
Author(s):  
Josef Prousek ◽  
Adolf Jurášek ◽  
Jaroslav Kováč
Keyword(s):  
Alkaline Medium ◽  
H Nmr ◽  
Phenyl Sulfone ◽  
Alkylation Reactions

5-Nitrofurfuryl bromide (I) and 4-nitrobenzyl bromide (VI) were investigated as possible alkylation reagents in reaction with 5-nitrofurfuryl trichloromethyl sulfone (IV) and 5-nitrofurfuryl phenyl sulfone (V). 1,2-Bis(5-nitro-2-furyl)ethylene (III) was formed from I in an alkaline medium and 1,2-bis(5-nitro-2-furyl)ethane (X) in the presence of furfuryl mercaptan. Products of this reaction were identified by IR, UV, 1H NMR and mass spectrometries.

Preparation and alkylation reactions of 4-nitrobenzyl and 5-nitrofurfuryl sulfones

1988 ◽  
Vol 53 (4) ◽  
pp. 851-856 ◽  
Author(s):  
Josef Prousek
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Mass Spectroscopy ◽  
Substitution Reaction ◽  
Reaction Medium ◽  
Polyethylene Glycols ◽  
H Nmr ◽  
Phenyl Sulfone ◽  
Alkylation Reactions

Substitution reaction of 5-nitrofurfuryl bromide (I) with sodium thiophenoxide and 4-chlorothiophenoxide in dimethyl sulfoxide at 20 °C and oxidation with dimethyl sulfoxide in the reaction medium afforded 5-nitrofurfuryl phenyl sulfone (IVa) and 5-nitrofurfuryl 4-chlorophenyl sulfone (IVb), respectively. Similarly, 4-nitrobenzyl bromide reacted with sodium 4-chlorothiophenoxide to give 4-nitrobenzyl 4-chlorophenyl sulfone (VII) and with sodium phenylsulfinate to afford 4-nitrobenzyl phenyl sulfone (IX). The sulfide intermediates were not isolated. The sulfone IX was used as substrate in alkylation reactions, catalysed by polyethylene glycols. Derivatives IVb and VII were identified by IR and mass spectroscopy, alkylation products by 1H NMR spectroscopy.

Structure reexamination of aliphatic nitrones and their dimers

1979 ◽  
Vol 44 (7) ◽  
pp. 2221-2229 ◽  
Author(s):  
Břetislav Princ ◽  
Otto Exner
Keyword(s):  
Alkaline Medium ◽  
Benzyl Chloride ◽  
Phenyl Group ◽  
H Nmr ◽  
Condensation Products ◽  
Alkylation Reactions

The structure of some compounds reported in the literature as nitrones II has been reexamined using mainly the 1H NMR and mass spectroscopies. The nitrone structure has been confirmed for the condensation products of N-alkylhydroxylamines with aldehydes (IIf) or ketones (IIj,l,m), as well as for the products of alkylation of aldoximes with benzyl chloride (IId,h). Other similar alkylation reactions yield generally a mixture of the nitrone and the dimeric oxazolidine derivative (Va,b,e), in addition to the O-alkylated oxime (VI). The nitrone is assumed to be the primary product in any case, its subsequent dimerization is promoted either by the alkaline medium or by the presence of a phenyl group as in Vg,k.

Study of keto-enol tautomerism and alkylation reactions of β-ketosulphones of 5-nitrofuran series

1981 ◽  
Vol 46 (12) ◽  
pp. 3115-3121 ◽  
Author(s):  
Adolf Jurášek ◽  
Dana Polakovičová ◽  
Jaroslav Kováč
Keyword(s):  
Methyl Iodide ◽  
Nmr Spectra ◽  
Chemical Investigation ◽  
Ch Acids ◽  
H Nmr ◽  
Methyl Derivatives ◽  
Alkylation Reactions

2-(5-Nitro-2-furyl)-2-oxoethyl 3-X-phenyl sulphones I react with diazomethane in tetrahydrofuran or dioxane to give trisubstituted ethylenes II, i.e. 1-(5-nitro-2-furyl)-1-methoxy-2-(4-X-phenylsulphonyl)ethylenes (X = H, CH3, OCH3, N(CH3)2, Cl, NO2) which have Z configuration. From results of spectral and chemical investigation it follows that β-ketosulphones of 5-nitrofuran series only exist in ketoform and are very strong CH-acids (pKa 7.82-5.23). Alkylation of the sulphones I (X = H, CH3) with methyl iodide under conditions of extraction alkylation gives the corresponding C-methyl derivatives III. Interpretation is given of IR, UV, 13C and 1H NMR spectra of the sulphones I and II.

Synthesis of 1,3-diazaspiro[5,5]undecanes and 1-thia-3-azaspiro[5,5]undec-2-enes by reaction of 2-cyanocyclohexylideneacetyl isothiocyanate with amines and sodium hydrogen sulfide

1987 ◽  
Vol 52 (4) ◽  
pp. 989-994 ◽  
Author(s):  
Milan Dzurilla ◽  
Ondrej Forgáč ◽  
Peter Kutschy ◽  
Pavol Kristian ◽  
Dušan Koščík ◽  
...  
Keyword(s):  
Hydrogen Sulfide ◽  
Alkaline Medium ◽  
Mass Spectroscopy ◽  
Aromatic Amines ◽  
Secondary Amines ◽  
H Nmr ◽  
Sodium Hydrogen ◽  
Elemental Analyses ◽  
Primary Aromatic Amines ◽  
C Nmr

2-Cyanocyclohexylideneacetyl isothiocyanate (II) reacts with sodium hydrogen sulfide to give 1-thia-3-azaspiro[5,5]undecane. Reaction of II with secondary amines afforded 1-thia-3-azaspiro[5,5]undec-2-enes whereas primary aromatic amines gave 1,3-diazaspiro[5,5]undecanes under the same conditions. Both types of reactions proceed via substituted thioureas which were isolated pure only in the case of 4-methylaniline and 4-methoxyaniline. They were cyclized in alkaline medium to the corresponding diazaspiro derivatives. The structure of the synthesized compounds was confirmed by their elemental analyses and IR, 1H NMR, 13C NMR and mass spectroscopy.

Regioselectivity in SNH reactions of some 3-nitro-1,5-naphthyridines with chloromethyl phenyl sulfone

2004 ◽  
Vol 82 (5) ◽  
pp. 567-570 ◽  
Author(s):  
Maria Grzegożek ◽  
Barbara Szpakiewicz
Keyword(s):  
Nmr Spectroscopy ◽  
Nucleophilic Substitution ◽  
Key Words ◽  
High Yield ◽  
Vicarious Nucleophilic Substitution ◽  
H Nmr ◽  
Phenyl Sulfone ◽  
Convenient Synthesis ◽  
Key Words 3 ◽  
Hydrogen Substitution

3-Nitro-1,5-naphthyridine and its 2-substituted derivatives react with the carbanion of chloromethyl phenyl sulfone to give hydrogen-substitution products at position 4 in high yield. The intermediacy of 4-(phenylsulfonyl)chloromethyl σ adducts of 2-R-3-nitro-1,5-naphthyridines (R = H, D, Cl, OC2H5, NHCH3, OH) was established by 1H NMR spectroscopy. A convenient synthesis of 2-N-methylamino-3-nitro-1,5-naphthyridine is reported. Key words: 3-nitro-1,5-naphthyridines, anionic (phenylsulfonyl)chloromethyl σ adducts, vicarious nucleophilic substitution.

5aH.10aH.15aH-Tribenzo [b.f.j] [1.4.7] trioxa [9 b] azaphenalene - vermeintliche Benzoxete / 5aH, 10aH, 15aH-Tribenzo[b,f,j][l,4,7]trioxa[9 b]azaphenalenes - Supposed Benzoxetes

1979 ◽  
Vol 34 (2) ◽  
pp. 290-296 ◽  
Author(s):  
Herbert Meier ◽  
Ahmed Issa ◽  
Ursula Merkle
Keyword(s):  
Alkaline Medium ◽  
Mass Spectroscopy ◽  
Structure Elucidation ◽  
H Nmr ◽  
Degradation Reactions ◽  
Polycyclic System ◽  
C Nmr

Abstract A supposed benzoxete is determined as a complex polycyclic system: cis,cis,cis-5 aH,10 aH,15 aH-tribenzo[b,f,j][1,4,7]trioxa[9 b]azaplienalene. The structure elucidation is performed by spectroscopycal methods (IR, 1H NMR, 13 C NMR and mass spectroscopy) and by degradation reactions in an acidic or an alkaline medium.

scholarly journals Anti-inflammatory properties of some novel thiazolo[4,5-b]pyridin-2-ones

Pharmacia ◽  
2020 ◽  
Vol 67 (3) ◽  
pp. 121-127
Author(s):  
Taras Chaban ◽  
Vasyl Matiychuk ◽  
Olexandra Komarytsya ◽  
Iryna Myrko ◽  
Ihor Chaban ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Paw Edema ◽  
H Nmr ◽  
Rat Paw Edema ◽  
Anti Inflammatory ◽  
Alkylation Reactions ◽  
Rat Paw ◽  
Inflammatory Action

Synthesis of novel N3 and C5 substituted thiazolo[4,5-b]pyridin-2-ones was carried out on the basis of [3+3]-cyclocodensation, acylation and alkylation reactions. The structures of the obtained compounds were confirmed by 1H NMR spectroscopy, and elemental analysis. The anti-inflammatory action of novel thiazolo[4,5-b]pyridine-2-one derivatives was evaluated in vivo employing the carrageenan-induced rat paw edema method. When compared with Ibuprofen, some our compounds were found to be more potent. Graphical abstract

Über die Koordination von Kohlenmonoxid an Bis(dithiolato)-Eisen-Komplexen [1] / On the Coordination of Carbon Monoxide on Bis(dithiolato)-Iron Complexes [1]

1978 ◽  
Vol 33 (2) ◽  
pp. 190-196 ◽  
Author(s):  
D. Sellmann ◽  
P. Kreutzer ◽  
E. Unger
Keyword(s):  
Carbon Monoxide ◽  
Solid State ◽  
Oxidation State ◽  
Alkaline Medium ◽  
Mass Spectra ◽  
Iron Complexes ◽  
Solution Temperature ◽  
H Nmr ◽  
Iron Salts ◽  
Elemental Analyses

The reaction of CO with iron salts in the presence of benzene-dithiol depends on the oxidation state of iron, pH of the solution, temperature and CO pressure. In alkaline EtOH one obtains labile cis-[Fe(CO)2(C6H4S2)2]2- complexes, which cannot be isolated in the solid state. On acidifying, oxidizing with O2 or heating the solution, the CO ligands are split off; after reduction with NaBH4, CO can be co-ordinated again at pH > 7 under normal conditions. Reacting benzene-1-thiomethyl-2-thiol in alkaline medium with Fe2+ and CO yields the isolable [cis-Fe(CO)2(CH3S-C6H4-S)2], which is characterized by elemental analyses, IR, 1H NMR and mass spectra. It is a labile complex coordinating CO reversibly

Das Verhalten der Körpermasse bei einem 81-jährigen Läufer an einem 100-km-Lauf

Praxis ◽  
2009 ◽  
Vol 98 (3) ◽  
pp. 143-149 ◽  
Author(s):  
Knechtle ◽  
Wirth ◽  
Knechtle ◽  
Kohler
Keyword(s):  
H Nmr

Ein 81-jähriger Läufer mit Status nach aortokoronarem Bypass bei bekannter koronarer Herzkrankheit hat einen 100-km-Lauf in 19 h und 45 min erfolgreich beendet. Vor und unmittelbar nach dem Lauf wurden Fett- und Muskelmasse nicht-invasiv sowohl mit der bioelektrischen Impedanzanalyse als auch mit der klassischen Hautfaltenmethode bestimmt. Zusätzlich wurden Blut- und Urinproben zur Beurteilung des Flüssigkeitshaushaltes genommen und eine ¹H-NMR-Spektroskopie des Urins zum Nachweis eines erhöhten Kohlenhydrat-, Fett- oder Eiweissstoffwechsels durchgeführt. Das Körpergewicht nahm um 1.9 kg ab. Während die errechnete Muskelmasse um 0.1 kg zunahm, nahm die errechnete Fettmasse um 0.2 kg (anthropometrische Methode) resp. 3.1 kg (BIA) ab. Das errechnete Körperwasser nahm um 1.2 l zu. Während Hämatokrit, Harnstoff und spezifisches Gewicht des Urins zunahmen, sank das Natrium im Blut ab. Das Plasmavolumen nahm um 19% ab. Die ¹H-NMR-Spektroskopie des Urins zeigte nach der Belastung einen Anstieg der Ketonkörper. Um einen Abbau der Muskelmasse objektivieren zu können, muss der Ausgangswert des Körperwassers abgewartet werden, um keine Fehlinterpretation aufgrund der Methoden zu machen. Unklar bleibt, wieso es zu einer Einlagerung von Wasser kam. In weiteren Untersuchungen könnten zusätzliche Methoden wie DEXA, Muskelbiopsien und Bestimmung von weiteren Blut- und Urinparametern Auskunft geben, ob effektiv und wie viel Muskelmasse abgebaut wird und ob Abbauprodukte der Muskulatur die Nierenfunktion einschränken und somit zu einer Wasserretention führen.

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