Some condensation products of ergoline - I Derivatives with ketones

1980 ◽  
Vol 45 (3) ◽  
pp. 755-760 ◽  
Author(s):  
Jiří Křepelka ◽  
Jiří Holubek ◽  
Miroslav Semonský
Keyword(s):  
Sulfuric Acid ◽  
Condensation Product ◽  
Condensation Products ◽  
Inhibiting Effect ◽  
Toluenesulfonic Acid ◽  
Cyclohexyl Ester ◽  
Acid Esterification ◽  
Derivatives Of

Monotopic bis-ergolin-2-yl derivatives of alkanes and cycloalkanes (I-VIII) were prepared on reaction of derivatives of ergoline-I (XI-XIV) with ketones in the presence of sulfuric acid or p-toluenesulfonic acid. Esterification of compound XV with cyclohexanol under catalysis with-p-toluenesulfonic acid gave condensation product IX after previous separation of cyclohexyl ester XVI. The condensation products did not exhibit prolactin inhibiting effect.

7-O-Alkyl derivatives of daunomycinone

1984 ◽  
Vol 49 (1) ◽  
pp. 313-319 ◽  
Author(s):  
Věra Přikrylová ◽  
Petr Sedmera ◽  
Josef V. Jizba ◽  
Jindřich Vokoun ◽  
Helena Lipavská ◽  
...  
Keyword(s):  
H Nmr ◽  
Toluenesulfonic Acid ◽  
Alkyl Derivatives ◽  
Derivatives Of

Reaction of daunomycinone (I) with alcohols and p-toluenesulfonic acid produces a mixture (~3 : 1) of its (7S)- and (7R)-O-alkyl derivatives II-IX. According to the 1H NMR evidence, the alicyclic ring exists in the 9H8 conformation in (7R)-O-alkyl derivatives, on the contrary to (7S)-epimers and 7-epi-daunomycinone that adopt the 8H9 conformation.

SYNTHESIS OF 1,1,1-TRICHLORO-2,2-BIS-(p-CYANOPHENYL)-ETHANE

1952 ◽  
Vol 30 (3) ◽  
pp. 203-207 ◽  
Author(s):  
Yvon Perron ◽  
Roger Barré
Keyword(s):  
Condensation Product ◽  
Starting Material ◽  
Derivatives Of

The synthesis of 1,1,1-trichloro-2,2-bis-(p-cyanophenyl)-ethane was carried out with the condensation product of chloral and toluene as starting material. This product was converted, through the corresponding tetraacetate, to 1,1,1-trichloro-2,2-bis-(p-aldehydophenyl)-ethane which in turn reacted with hydroxylamine to give the dioxime. The subsequent dehydration of the latter gave rise to the desired dinitrile. The corresponding dichloro derivatives of the oxime and nitrile were also prepared.

Synthèse de quelques dérivés du tétrahydro-4,5,6,7 benzothiazoline-Δ2α-acétate d'éthyle

1968 ◽  
Vol 46 (23) ◽  
pp. 3643-3648 ◽  
Author(s):  
Réal Laliberté ◽  
Hilda Warwick ◽  
Georges Médawar
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Spectroscopic Evidence ◽  
Concentrated Sulfuric Acid ◽  
Derivatives Of

Some derivatives of α-cyano tétrahydro benzothiazoline-Δ2α-acetic acid and their intermediates are described. The lack of reactivity of this class of compounds and products of treatment with concentrated sulfuric acid have been studied. Assignment of configuration was based on infrared and ultraviolet spectroscopic evidence.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

STUDIES ON LIGNIN AND RELATED COMPOUNDS: XVI. PHENOL LIGNIN FROM SPRUCE WOOD, FROM FREUDENBERG SPRUCE LIGNIN AND WILLSTÄTTER SPRUCE LIGNIN

1935 ◽  
Vol 13b (2) ◽  
pp. 61-77 ◽  
Author(s):  
Irene Koerber Buckland ◽  
Fritz Brauns ◽  
Harold Hibbert
Keyword(s):  
Condensation Product ◽  
Analytical Data ◽  
Insoluble Fraction ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Condensation Products ◽  
Building Unit ◽  
Spruce Wood ◽  
Analytical Results ◽  
The Difference

The condensation of lignin with phenol by treatment of spruce wood meal with this solvent, using hydrogen chloride as catalyst, yields two chemically different phenol lignins, namely, an ether-insoluble and an ether-dioxane–soluble phenol lignin, in a ratio of approximately 3 to 1. Duplicate preparations gave the same yields of these two fractions, analyses of which gave concordant results, indicating homogeneity and constancy of composition.The analytical results of the ether-insoluble phenol lignin, and of its methylated and acetylated derivatives, can be interpreted on the basis of the Brauns–Hibbert formula for the "native" lignin unit. It is found, in this way, that the ether-insoluble phenol lignin contains three new free phenolic hydroxyl groups capable of methylation with diazomethane, while one phenol group has reacted with one hydroxyl group in the lignin unit with formation of a phenyl-oxygen ether linkage.The analytical results of the ether-dioxane–soluble phenol lignin indicate that a much larger quantity of phenol has condensed with the "native" lignin building unit than in the case of the ether-insoluble fraction. The exact number of phenol molecules reacting to form this condensation product has not been determined experimentally although calculations based on analytical data point to a number as large as 15 or 21.The phenol condensation products were obtained from Freudenberg and Willstätter lignins in nearly quantitative yield and found to differ from the directly extracted phenol lignin in that neither of them could be resolved into two fractions, thus indicating that some change had taken place in the native lignin during the isolation process. The Brauns-Hibbert formula can also be applied to interpret the experimental data in both cases. These lignins appear to contain the same fundamental building unit as the ether-insoluble phenol lignin fraction isolated directly from spruce wood, with the difference that the former probably have one additional hydroxyl group capable of acetylation and diazomethane-methylation.The correlation found to exist in the present investigation between the phenol condensation products from native spruce lignin, isolated Freudenberg lignin and Willstätter lignin is regarded as providing definite experimental evidence indicating the presence of a chemical unit common to various lignins. The phenol condensation products, it is considered, may serve as valuable reference compounds for proving the identity of lignins obtained from different sources and by use of different chemical reagents.

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