Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide

2020 ◽  
Vol 75 (6-7) ◽  
pp. 697-708
Author(s):  
Willi Kantlehner ◽  
Heinz Malik ◽  
Ralf Kreß
Keyword(s):  
Formic Acid ◽  
Carbonic Acid ◽  
Sodium Hydride ◽  
Counter Ions ◽  
Carbon Acids ◽  
Ionische Flüssigkeiten ◽  
Derivatives Of ◽  
Elemental Iodine ◽  
Guanidinium Salt ◽  
Guanidinium Salts

AbstractCyclopropylacetylene and N,N,N′,N′,N′′,N′′-hexamethylguanidinium chloride (1a) react to give the orthoamide derivative 8c, in the presence of sodium hydride. 8c is transformed by elemental iodine to the vinylogous guanidinium salt 6f. Anion metathesis with the salts 5a, 5e, 6g delivers vinylogous guanidinium salts 5e–5i, 12a with counter ions derived from carbon acids (tricyanomethane, 1,1,3,3-tetracyano-propene). Phenylogous amidinium salts 15 guanidinium salts 19, 21 and the phenylogous orthoamide derivatives of formic acid 18 and carbonic acid 33 have been prepared.

scholarly journals Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates

2014 ◽  
Vol 10 ◽  
pp. 2255-2262 ◽  
Author(s):  
Jan Szabo ◽  
Kerstin Karger ◽  
Nicolas Bucher ◽  
Gerhard Maas
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Intermolecular Hydrogen Bonds ◽  
Aryl Isocyanates ◽  
Borane Reduction ◽  
Solid State Structures ◽  
Aryl Isothiocyanates ◽  
Derivatives Of ◽  
Guanidinium Salt ◽  
Guanidinium Salts

1,2,3-Triaminoguanidinium chloride was combined with benzaldehyde and hydratropic aldehyde to furnish the corresponding tris(imines), which were converted into 1,2,3-tris(benzylamino)guanidinium salts by catalytic hydrogenation in the former, and by borane reduction in the latter case. The resulting alkyl-substituted triaminoguanidinium salts underwent a threefold carbamoylation with aryl isocyanates to furnish 1,2,3-tris(ureido)guanidinium salts, while p-toluenesulfonyl isocyanate led only to a mono-ureido guanidinium salt. With aryl isothiocyanates, 3-hydrazino-1H-1,2,4-triazole-5(4H)-thione derivatives were obtained. Compounds 7a and 8 show interesting solid-state structures with intra- and intermolecular hydrogen bonds.

Binding of calcium and lead ions to carboxystarch prepared by action of nitrogen dioxide on native starch and its 2,3-dialdehyde derivatives

1986 ◽  
Vol 51 (6) ◽  
pp. 1340-1351 ◽  
Author(s):  
Rudolf Kohn ◽  
Karol Tihlárik
Keyword(s):  
Nitrogen Dioxide ◽  
Alkaline Medium ◽  
Binding Capacity ◽  
Lead Ions ◽  
Carbonyl Groups ◽  
Weakly Alkaline ◽  
Exchange Cations ◽  
Counter Ions ◽  
The Stability ◽  
Derivatives Of

The binding of calcium and lead ions to carboxy derivatives of starch prepared by allowing nitrogen dioxide to act on native maize starch (procedure A) and on starch 2,3-dialdehyde derivatives of degrees of oxidation DO(d.a.) ≥ 0.94 (procedure B) was studied. The carboxy group content of the samples in the H+ form was 4.6 - 12.1 mmol g-1. The effect of alkaline medium on the stability of the carboxy derivatives and on their ability to bind and exchange cations was examined. The Ca2+ → 2K+ exchange was evaluated in terms of the decrease in the electrostatic free enthalpy Δ(Gel/N)KCa, determined by alkalimetric potentiometric titrations, and the binding of Pb2+ ions was evaluated in terms of the activity of the Pb2+ counter-ions determined in suspensions of Pb salts of the carboxy derivatives by means of an ion specific electrode. The IR and CD spectra revealed that the carboxystarch preparations obtained by procedure A contained, in addition to free carboxy groups, a considerable amount of carbonyl groups. During the conversion of the latter groups to the former, even in a weakly alkaline medium, the carboxy derivatives undergo an appreciable degradation and lose, to a great extent, their ability to bind and exchange cations. Procedure B, on the other hand, leads to highly selective starch and amylose carboxy derivatives, exhibiting a small amount of carbonyl groups and featuring a relative stability towards alkaline medium; their binding capacity is as high as 12 milliequivalents of cations per g of sample.

Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen

2020 ◽  
Vol 75 (6-7) ◽  
pp. 685-695
Author(s):  
Willi Kantlehner ◽  
Ioannis Tiritiris ◽  
Wolfgang Frey ◽  
Ralf Kreß
Keyword(s):  
Crystal Structure ◽  
Guanidinium Salt ◽  
Guanidinium Salts

AbstractBis[bis(dibutylamino)methylen]hydrazine 8 is prepared from N,N,N′,N′-tetrabutylchloroformamidinium chloride (4c) and hydrazine. Bromine transforms 8 to the heterocyclic guanidinium salt 15a which is isolated as tetraphenylborate. From N,N,N′,N′-tetraalkylchloroformamidiniumchlorides and ethylendiamine the diguanidines are prepared which are alkylated to give diguanidinium salts, From these salts guanidinium salts can be prepared by anion metathesis with tetraphenylborate-, iodide-, hexafluorphosphate-, trifluoromethansulfonat-, bis(trifluormethansulfonyl)imide and tricyanmethanide as counteranions. The structure of the compounds 15 and 17b is confirmed by crystal structure analyses.

Preliminary Note on Dietthio and Diethylsulphone derivatives of Succinic Acid

1897 ◽  
Vol 21 ◽  
pp. 156-159
Author(s):  
Crum Brown ◽  
R. Fairbairn
Keyword(s):  
Succinic Acid ◽  
Calcium Chloride ◽  
Boiling Point ◽  
Carbonic Acid ◽  
Steam Bath ◽  
Sodium Bromide ◽  
Absolute Alcohol ◽  
Preliminary Note ◽  
Aqueous Layer ◽  
Derivatives Of

Sodium mercaptide and dibromosuccinic ether, in the proportion of two molecules of the former to one of the latter, were dissolved separately in absolute alcohol, and slowly mixed. A considerable evolution of heat took place, while sodium bromide separated out. The flask was then digested for some hours on the steam-bath. The alcohol was subsequently distilled off, and the residue, on cooling, was treated with water. An oil separated out. This oil was collected by means of a separating funnel, and the aqueous layer several times extracted with ether. The oil and the ethereal extracts were added together and dried over calcium chloride. Next morning the ether was distilled off at the ordinary pressure. The remainder was distilled in vacuo. Between 50° and 60° a few drops came over, which proved to be ethyldisulphide.The remainder came over between 150° and 170°.This latter fraction was redistilled, and a portion of it used for analysis. The boiling point at 20 mm. pressure was 160°.Combustion of dietthiosuccinic ether.Weight of substance taken = ·2477 gram.Weight of carbonic acid obtained = ·4476 gram.Weight of water obtained = ·1702 gram.

Synthesis and Biological Effects of N-(2-Phosphonomethoxyethyl) Derivatives of Deazapurine Bases

1993 ◽  
Vol 58 (6) ◽  
pp. 1419-1429 ◽  
Author(s):  
Hana Dvořáková ◽  
Antonín Holý
Keyword(s):  
Biological Effects ◽  
Sodium Hydride ◽  
Cesium Carbonate ◽  
Cytostatic Effect ◽  
Phosphonic Acids ◽  
Dna Viruses ◽  
Purine Bases ◽  
Heterocyclic Bases ◽  
L 1210 Leukemia ◽  
Derivatives Of

Analogs of antiviral 9-(2-phosphonomethoxyethyl)adenine (PMEA,II), containing modified purine bases 1-deazaadenine (VII, 3-deazapurine (XI), 7-deaza-7-cyanoadenine (XIIIb) and 3-deazaguanine (XXIb) were prepared by alkylation of the heterocyclic bases with bis(2-propyl) 2-chloroethoxymethylphosphonate (V) in dimethylformamide in the presence of sodium hydride or cesium carbonate. The obtained protected derivatives were deblocked with bromotrimethylsilane to give the phosphonic acids. 3-DeazaPMEG (XXIb) is active against DNA viruses and exhibits a marked cytostatic effect against L-1210 leukemia.

Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis

1999 ◽  
Vol 54 (9) ◽  
pp. 1133-1137
Author(s):  
Astrid Knieß ◽  
Margit Gruner ◽  
Roland Mayer
Keyword(s):  
Carbonyl Group ◽  
Carbonic Acid ◽  
Ester Group ◽  
Reaction Behavior ◽  
Anthracene Derivatives ◽  
Sterical Hindrance ◽  
Derivatives Of

ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anthracenyl)-2-(dimethylamino)methylen-3-oxo-propionate (11) with hydrazine hydrochlorides gives 4-(9-anthracenoyl)-5-hydroxy-pyrazoles (14). This is caused by the sterical hindrance of the carbonyl group of the anthracene derivatives in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the enaminone 11.

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