Synthesis of 1,2,4-triazine-3,5(2H,4H)-diones containing electronegative substituents in position 6

1983 ◽  
Vol 48 (9) ◽  
pp. 2676-2681 ◽  
Author(s):  
Jiří Farkaš
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Nitro Compound ◽  
Trifluoroacetic Acid ◽  
Acid Synthesis ◽  
Amino Derivative ◽  
Effect Of Substituents ◽  
Fluoro Derivative ◽  
Cuprous Cyanide ◽  
Derivatives Of

Reaction of fluorine with 1,2,4-triazine-3,5(2H,4H)-dione (I) in acetic acid afforded the 6-fluoro derivative II in low yield. The 6-nitro compound III was prepared by oxidation of the 6-amino derivative of compound I with hydrogen peroxide in trifluoroacetic acid. Synthesis of the 6-cyano compound IV was accomplished by treatment of the 6-bromo derivative with cuprous cyanide in N,N,N',N'-tetramethylurea. The effect of substituents on the carbonyl frequencies for 6-substituted derivatives of I was studied.

New derivatives of xanthenone-4-acetic acid: Synthesis, pharmacological profile and effect on TNF-α and NO production by human immune cells

2006 ◽  
Vol 14 (12) ◽  
pp. 4101-4109 ◽  
Author(s):  
Silvia Gobbi ◽  
Federica Belluti ◽  
Alessandra Bisi ◽  
Lorna Piazzi ◽  
Angela Rampa ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Immune Cells ◽  
Acid Synthesis ◽  
No Production ◽  
Pharmacological Profile ◽  
Tnf Α ◽  
Human Immune ◽  
Derivatives Of

A new method for the preparation of peroxymonophosphoric acid

2003 ◽  
Vol 81 (2) ◽  
pp. 156-160 ◽  
Author(s):  
Tian Zhu ◽  
Hou-min Chang ◽  
John F Kadla
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Carbon Tetrachloride ◽  
Glacial Acetic Acid ◽  
Acid Synthesis ◽  
Conversion Ratio ◽  
New Method ◽  
Phosphorous Pentoxide ◽  
Preparation Conditions ◽  
Peroxy Acids

A new method for the preparation of peroxymonophosphoric acid (H3PO5) has been developed. It utilizes a biphasic solution to moderate the vigorous reaction between phosphorous pentoxide (P2O5) and hydrogen peroxide (H2O2). P2O5 is suspended in carbon tetrachloride (CCl4), and concentrated H2O2 is slowly added while being vigorously stirred at low temperature. Careful control of the reaction temperature through the slow addition of H2O2 is critical. Using typical preparation conditions (P2O5:H2O2 = 0.5:1, H2O2 70 wt %, 2°C, 120–180 min), ~70% of the H2O2 is effectively converted to H3PO5. Increasing the concentration of H2O2, as well as the mole ratio of P2O5:H2O2, leads to an even higher % conversion of H2O2 to H3PO5. The addition of glacial acetic acid to the P2O5:H2O2 suspension at the end of the 120–180 min reaction (P2O5:H2O2:CH3COOH = 0.5:1:0.3) leads to the formation of peracetic acid in addition to H3PO5, and to an overall increase in the conversion ratio of total peroxy acids based on H2O2 (>95%).Key words: peroxymonophosphoric acid, synthesis, stability, conversion ratio.

ChemInform Abstract: New Derivatives of 2-(3,5-Dioxo-4-azatricyclo [5.2.1.02,6-endo]dec-8-en-4-yl)acetic Acid. Synthesis and Reactivity.

ChemInform ◽  
2008 ◽  
Vol 39 (10) ◽  
Author(s):  
I. N. Tarabara ◽  
Ya. S. Bondarenko ◽  
A. A. Zhurakovskii ◽  
L. I. Kas'yan
Keyword(s):  
Acetic Acid ◽  
Acid Synthesis ◽  
Derivatives Of

New derivatives of 2-(3,5-Dioxo-4-azatricyclo[5.2.1.02,6-endo ]dec-8-en-4-yl)acetic acid. Synthesis and reactivity

2007 ◽  
Vol 43 (9) ◽  
pp. 1297-1304 ◽  
Author(s):  
I. N. Tarabara ◽  
Ya. S. Bondarenko ◽  
A. A. Zhurakovskii ◽  
L. I. Kas’yan
Keyword(s):  
Acetic Acid ◽  
Acid Synthesis ◽  
Derivatives Of

Acid-catalyzed migration of N4-acyl groups in cytosine derivatives

1979 ◽  
Vol 44 (6) ◽  
pp. 1819-1827 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Acetic Acid ◽  
Trifluoroacetic Acid ◽  
The Other ◽  
Aqueous Acetic Acid ◽  
Amino Group ◽  
Benzoyl Group ◽  
Benzoyl Cyanide ◽  
Acid Catalyzed ◽  
Derivatives Of ◽  
Anhydrous Acetic Acid

Heating 1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)-N4-benzoylcytosine (I) in 80% acetic acid afforded 1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)-N3-benzoylcytosine (II). Benzoylation of 5'-O-tritylcytidine (V) led to the 2',3',N4-tribenzoyl derivative VI which was refluxed with 80% acetic acid to give 2',3',N3-tribenzoylcytidine (VII). Analogously, 2',3',5',N4-tetrabenzoylcytidine (IX), prepared by benzoylation of cytidine with benzoyl cyanide, gave on reflux with 80% acetic acid 2',3',5',N3-tetrabenzoylcytidine (X). Under identical conditions, 1-methyl-N4-benzoylcytosine (XI) afforded directly 1-methyluracil (XII) .This migration takes place also in acetyl derivatives of cytosine nucleosides: 2',3',5',N4-tetraacetylcytidine (XIII) was transformed to the N3-acetylcytosine derivative XIV. On the other hand, migration of acetyl or benzoyl group from the exo-amino group of adenine has not been observed under the mentioned conditions. The migration of the N4-acyl group of cytosine derivatives proceeds best in aqueous acetic acid, more slowly also in anhydrous acetic acid, but not by action of trifluoroacetic acid in 1,2-dichloroethane.

Highly polar potential metabolites of the neuroleptic agent oxyprothepin: Synthesis of 2-hydroxy-8-methylsulfonyl and 3-hydroxy-8-methylsulfonyl derivatives of 10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin

1985 ◽  
Vol 50 (2) ◽  
pp. 519-537 ◽  
Author(s):  
Jiří Jílek ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Schlanger ◽  
Josef Pomykáček ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Potassium Carbonate ◽  
Neuroleptic Agent ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Methoxybenzoic Acid

The acid XI, obtained by reaction of (2-iodo-5-methoxyphenyl)acetic acid with 4-(methylsulfonyl)thiophenol (VIII) in dimethylformamide in the presence of potassium carbonate and copper, was transformed via intermediates XIIa-XIVa to compound XVa. Demethylation with boron tribromide afforded compound III, the potential metabolite of oxyprothepin (II). Its oxidation with hydrogen peroxide in acetic acid gave the sulfoxide XVII, which is a further potential metabolite. A reaction of 2-iodo-4-methoxybenzoic acid with VIII and potassium carbonate in dimethylformamide in the presence of copper afforded the acid XIX whose ester XXI was reduced with diborane to the alcohol XXII; hydrogenolysis to compound XXIII was also observed. The alcohol XXII was processed via compounds XXIV and XXV to the acid XXVI which was cyclized in a low yield to the ketone XIIb. A further processing via the intermediates XIIIb and XIVb led to compound XVb. Demethylation gave compound IV, another potential metabolite.

Research on Modified Rubbers. Part IV. The Oxidation of Rubber with Aqueous Hydrogen Peroxide-Acetic Acid Mixtures

1934 ◽  
Vol 7 (3) ◽  
pp. 454-461
Author(s):  
G. F. Bloomfield ◽  
E. H. Farmer
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Peracetic Acid ◽  
Glacial Acetic Acid ◽  
Chloroform Solution ◽  
Effective Control ◽  
Acid Mixture ◽  
Hydroxyl Groups ◽  
Derivatives Of ◽  
Degree Of Degradation

Abstract Mair and Todd (J. Chem. Soc., 1932,, 386), in extending the earlier work of Robertson and Mair (J. Soc. Chem. Ind., 46, 41T (1927)), studied the interaction of a chloroform solution of purified rubber with concentrated hydrogen peroxide (100 vols.) dissolved in glacial acetic acid; by this means they obtained a non-acidic substance of the empirical formula C50H92O16, which was unsaturated toward bromine and permanganate, and was considered to have all its oxygen present in the form of hydroxyl groups. Other workers have reported that when peracetic acid dissolved in glacial acetic acid is used in place of the hydrogen peroxide—acetic acid mixture, the products of reaction are acetylated derivatives of rubber (British Patent 369,716). These acetylated derivatives are stated to be obtainable either from solid rubber or from solutions of rubber, but no evidence as to their constitution has been advanced. Now the oxidative degradation of rubber is of considerable interest from two points of view: first, with regard to the light which it may throw on the size, structure, homogeneity, and normality of chemical behavior of the molecules of rubber; and, second, with regard to its efficacy as a means of transforming rubber into derivatives of similar or smaller molecular weight, capable of useful application in industry. The very careful work of Mair and Todd has gone far to show that hydrogen peroxide under the conditions of their experiments attacks the unsaturated centers of the rubber molecule and effects more or less complete hydroxylation of the carbon chain; at the same time it brings about a considerable degree of degradation of the molecule. The product of Mair and Todd, however, is produced under rather restricted conditions of reaction and the reagents employed are costly; consequently the extent to which the character of the product can be modified (i. e., by controlling the degree of degradation, hydroxylation, and acetylation) is left undetermined, and the possibility of producing useful materials at a reasonably low cost by modifying the conditions of reaction and the form of reactants is left unexplored. On the other hand, the employment of peracetic acid as an oxidizing agent, though offering a theoretically elegant way of effecting hydroxylation or acetoxylation at the unsaturated centers of the rubber molecule, is not without drawbacks: the preparation of the reagent is expensive and on a large scale dangerous; moreover, in spite of the fact that it is claimed to be employable either with solutions of rubber or with solid rubber, its reaction with rubber is so vigorous that the prospect of exercising any effective control over the extent of degradation or degree of hydroxylation (acetoxylation) is greatly diminished.

Chemistry of meso-Dimethylaminopropenyl- porphyrins and -bisporphyrins: the Synthesis of Australochlorin, a Benzochlorin Isomer.

1997 ◽  
Vol 50 (5) ◽  
pp. 487 ◽  
Author(s):  
Dmitry V. Yashunsky ◽  
Gelii V. Ponomarev ◽  
A. S. Moskovkin ◽  
Dennis P. Arnold
Keyword(s):  
Acetic Acid ◽  
Double Bond ◽  
Trifluoroacetic Acid ◽  
Membered Ring ◽  
Macrocyclic Complexes ◽  
Exocyclic Double Bond ◽  
Derivatives Of

The nickel(II) complex of meso-dimethylaminoprop-1-enyloctaethylporphyrin (2c) was converted by quaternization and thermolysis into a pair of novel isomeric macrocyclic complexes (3) and (4). These have a fused six-membered ring, and an exocyclic double bond on the neighbouring β-position, and have been named ‘australochlorins’. Heating these compounds in acetic acid leads to the known nickel(II) octaethylbenzochlorin (1) and a novel β-(1-acetoxyethyl)benzochlorin (5). Trifluoroacetic acid promotes the regioselective formation of benzochlorin/porphyrin species from the mononickel(II) complexes of the acrolein derivatives of bis(octaethylporphyrinyl)ethane and trans-ethene.

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