scholarly journals An Unusual Course of a Nitro Sugar Acetylation: Formation of a Crystalline Nitronic Acid – Acetic Acid Mixed Anhydride

1971 ◽  
Vol 49 (19) ◽  
pp. 3236-3238 ◽  
Author(s):  
Werner Rank ◽  
Hans H. Baer
Keyword(s):  
Acetic Acid ◽  
Acetyl Chloride ◽  
Acetyl Derivative ◽  
Acid Anhydride ◽  
Mixed Anhydride ◽  
Nitronic Acid

Whereas acetylation of methyl 4,6-O-benzylidene-3-deoxy-3-nitro-β-D-mannopyranoside (1) and its β-D-galacto isomer 2 with acetyl chloride and triethylamine in ether furnished the expected 2-O-acetylated nitro glycosides, 1a and 2a, the same method applied to the α-D-talo isomer 3 gave the 2-O-acetyl derivative of the corresponding nitronic acid – acetic acid anhydride, 4.

Potential nootropic agents: Synthesis of some (2-oxo-1-pyrrolidinyl)acetamides and some related compounds

1990 ◽  
Vol 55 (11) ◽  
pp. 2756-2764 ◽  
Author(s):  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Martin Valchář ◽  
Ivan Krejčí ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Survival Time ◽  
Acetyl Chloride ◽  
The Other ◽  
Anticonvulsant Effect ◽  
Mixed Anhydride ◽  
Ester Exchange ◽  
Nootropic Agents ◽  
The One ◽  
Related Compounds

Ethyl (2-oxo-1-pyrrolidinyl)acetate was transformed by ester exchange to the 2-dimethylaminoethyl ester VI which was converted to the choline iodide ester VII. The mixed anhydride of (2-oxo-1-pyrrolidinyl)acetic acid and monoethyl carbonate was reacted with ethyl aminoacetate to give the ester VIII which was transformed on the one hand to the amide IX, and to the 2-dimethylaminoethyl ester X on the other. Reaction of the latter with methyl iodide afforded a further choline iodide ester XI. Reactions of (2-oxo-1-pyrrolidinyl)acetyl chloride with 4-chloroaniline and 3-aminopyridine gave the amides XII and XIV. The anilide XIII was obtained from 2-(2-oxo-1-pyrrolidinyl)butyric acid and 4-chloroaniline by means of dicyclohexylcarbodiimide. The benzo analogue (XV) of piracetam (I) was synthesized from oxindole via the ester XVI. The anilide XII (V⁄FB-16 536) was found to potentiate significantly the anticonvulsant effect of diazepam in mice, to prolong the survival time of mice under conditions of nitrogen anoxia, and to prolong significantly the duration of the "gasping reflex" in mice.

Hot-Tube Reactions of Dehydroabietic Acid with Ketene-Producing Reagents. Pyrolysis of the Acid Chloride and Symmetrical and Mixed Anhydride Derivatives of Dehydroabietic Acid

1973 ◽  
Vol 51 (19) ◽  
pp. 3236-3241 ◽  
Author(s):  
Ray F. Severson ◽  
Walter H. Schuller
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Acid Chloride ◽  
Acetyl Chloride ◽  
Dehydroabietic Acid ◽  
Mixed Anhydride ◽  
Temperature Range ◽  
Acid Isomerization ◽  
Derivatives Of ◽  
Isopropenyl Acetate

Dehydroabietic acid (1a) was reacted with diketene, acetic acid, acetic anhydride, isopropenyl acetate, acetyl chloride, and acetone on Vycor rod at 450 °C in a hot tube. Dehydroabietic anhydride (1b) and acetyl dehydroabietate (1c) were pyrolyzed at 450 °C and dehydroabietyl chloride (1d) was pyrolyzed over a temperature range of 290–500 °C. The major olefin products resulting from decarboxylation of the various derivatives were 19-norabieta-4,8,11,13-tetraene (2), 19-norabieta-4(18),8,11,13-tetraene (3), 19-norabieta-3,8,11,13-tetraene (4), and cis-1,10a-dimethyl-7-isopropyl-1,2,3,9,10,10a-hexahydrophenanthrene (5). High conversions to these compounds were obtained. In the presence of the ketene-producing reagents the olefins were oxidized to yield substantial amounts of retene (6), compounds 2 and 5 being the most readily dehydrogenated. The acid isomerization of 2, 3, 4, and 5 was studied using p-toluenesulfonic acid in toluene at 110 °C.

Acetylation and Formylation of 3-Ferrocenylpyrroles

1999 ◽  
Vol 64 (1) ◽  
pp. 99-106
Author(s):  
Battsengel Gotov ◽  
Štefan Toma ◽  
Eva Solčániová
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aluminum Chloride ◽  
Acetyl Chloride ◽  
Trifluoroacetic Anhydride ◽  
Acid Mixture ◽  
Chloride Method

Acetylations of 3-ferrocenyl-1-methylpyrrole as well as 3-cyano-4-ferrocenylpyrrole and 3-cyano-4-ferrocenyl-1-methylpyrrole were performed. The course of the acylation is highly dependent on the acylation agent, that is acetyl chloride/aluminum chloride (method A), trifluoroacetic anhydride-acetic acid mixture (method B) or acetic anhydride/Sc(OTf)3 (method C). Method A gives the acetylation on ferrocene moiety, method B affords the trifluoroacetylation on pyrrole moiety and method C affords pyrrole moiety acetylation. Vielsmeier-Haack formylation gives the products of substitution on pyrrole moiety.

Synthesis of 2-oxo and 2-thioxo-3(2H)-benzothiazoleethanimic acid anhydride with acetic acid and related products

1988 ◽  
Vol 25 (5) ◽  
pp. 1503-1509 ◽  
Author(s):  
John J. D'Amico ◽  
Frederic G. Bellinger ◽  
John J. Freeman
Keyword(s):  
Acetic Acid ◽  
Acid Anhydride

Steroid and bile acids amide conjugates with D-glucosamine

2011 ◽  
Vol 76 (1) ◽  
pp. 65-74
Author(s):  
Zdena Nováková ◽  
Jana Tomanová ◽  
Lucie Štěrbová ◽  
Pavel Drašar
Keyword(s):  
Acetic Acid ◽  
Bile Acids ◽  
Acid Chloride ◽  
Acetyl Chloride ◽  
Glucosamine Hydrochloride ◽  
Negative Results ◽  
Step Procedure ◽  
One Step ◽  
New Type

New type of amide conjugates of steroid and bile acids with D-glucosamine 1 and 2 were prepared. Title compounds are prepared via acid chloride or using N-[({[(1E)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)(dimethylamino)methylidene]-N-methylmethanaminium tetrafluoroborate as condensation agent. They were examined for gelation properties with negative results. Per-O-acetylated D-glucosamine hydrochloride was prepared in one step procedure from D-glucosamine hydrochloride by acetylation in a mixture of acetyl chloride and acetic acid.

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