Heterocyclic Synthesis With Azides. I. The Reaction of Hydrazoic Acid With Ethoxymethylenemalonate

1992 ◽  
Vol 45 (10) ◽  
pp. 1571 ◽  
Author(s):  
A Donkor ◽  
RH Prager ◽  
MJ Thompson
Keyword(s):  
Sodium Azide ◽  
Trifluoroacetic Acid ◽  
Hydrazoic Acid ◽  
Heterocyclic Synthesis ◽  
Product Structures ◽  
Diethyl Ethoxymethylenemalonate

Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20� gives ethyl 5-ethoxyisoxazole-4-carboxylate (67%), diethyl cyanomalonate (21%) and diethyl ethoxyaminomethylenemalonate (5%). The last compound and its tautomer are converted into ethyl 1-ethoxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate. The product structures have been confirmed by synthesis or degradation.

Heterocyclic Synthesis With Azides. II. The Reaction of Azide With Ethoxymethylenemalonate

1992 ◽  
Vol 45 (11) ◽  
pp. 1781 ◽  
Author(s):  
A Donkor ◽  
RH Prager ◽  
MR Taylor ◽  
MJ Thompson
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Sodium Azide ◽  
Crystal Structure Analysis ◽  
Heterocyclic Synthesis ◽  
X Ray ◽  
Diethyl Ethoxymethylenemalonate

Sodium azide reacts with diethyl ethoxymethylenemalonate in dimethylsulfoxide to give diethyl 2,4-diethoxycarbonylpent-2-enedioate (12%) and diethyl 5-hydroxypyrrole-2,4-dicarboxyiate (60%). The structure of the latter was determined by X-ray crystal structure analysis at 150 K, and both compounds have been independently synthesized.

Heterocyclic Synthesis With Azides. III. Reactions of Triazolines Made From Arylmethylidenemalonates

1994 ◽  
Vol 47 (7) ◽  
pp. 1375 ◽  
Author(s):  
RH Prager ◽  
P Razzino
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Azide ◽  
Trifluoroacetic Acid ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Heterocyclic Synthesis

Ethyl alkylidenemalonates reacted with sodium azide in dimethyl sulfoxide to give principally triazoles via the first-formed 4,5-dihydro-1H-1,2,3-tiriazoles. The triazolines themselves, and other compounds derived from them, were isolated in trace amounts. Ethyl alkylidenemalonates combined with benzyl azide in a 1,3-dipolar cycloaddition reaction to give 1-benzyl-4,5-dihydro-1H-1,2,3-triazoles. When treated with potassium t- butoxide in dimethyl sulfoxide , these adducts either aromatized to the corresponding triazoles, underwent deethoxycarbonylation but did not aromatize, or lost nitrogen to give ethyl benzylaminomethylidenemalonates. The proclivity for each of these three processes was determined by the C5 substituent of the 4,5-dihydro-1H-1,2,3-triazole. Treatment of the 1-benzyl-4,5-dihydro-1H-1,2,3-triazoles with trifluoroacetic acid gave ethyl diazomalonate.

ChemInform Abstract: CATALYTIC POLAROGRAPHIC WAVES OF COBALT(II) IN SODIUM AZIDE WITH HYDRAZOIC ACID

1981 ◽  
Vol 12 (44) ◽  
Author(s):  
R. TOKORO ◽  
E. A. NEVES
Keyword(s):  
Sodium Azide ◽  
Hydrazoic Acid

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides

2016 ◽  
Vol 69 (1) ◽  
pp. 61 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis
Keyword(s):  
Ethyl Acetate ◽  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Acid ◽  
Sulfonic Acid ◽  
Trifluoroacetic Anhydride ◽  
Ring Cleavage ◽  
Thermal Rearrangement ◽  
Heterocyclic Synthesis ◽  
Similar Treatment ◽  
Catalytic Hydrogenolysis

Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

Catalytic polarographic wave of cobalt(II) in sodium azide with hydrazoic acid

1981 ◽  
Vol 125 (1) ◽  
pp. 115-128 ◽  
Author(s):  
Roberto Tokoro ◽  
Eduardo A. Neves
Keyword(s):  
Sodium Azide ◽  
Hydrazoic Acid ◽  
Polarographic Wave

γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of Biologically Active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones

2002 ◽  
Vol 57 (6) ◽  
pp. 668-676 ◽  
Author(s):  
Ashraf A. F. Wasfy ◽  
Mohamed M. H. Arief ◽  
Mahassen S. Amine ◽  
Shafey G. Donia ◽  
Aly A. Aly
Keyword(s):  
Hydrazine Hydrate ◽  
Sodium Azide ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
Secondary Amines ◽  
Keto Acid ◽  
Heterocyclic Synthesis ◽  
Reaction Conditions ◽  
Carbon Nucleophiles ◽  
Pyrazolone Derivative

α-Benzylamino-β-(5,5-dioxodibenzothiophen-2-carbonyl)propionic acid (1) has been synthesized by treating the corresponding β-aroylacrylic acid with benzylamine in dry benzene. On treatment with hydrazine hydrate the keto acid 1 furnishes the corresponding pyridazinone derivative 2. The behaviour of 2 towards carbon electrophiles, namely, ethyl chloroacetate, acrylonitrile, formaldehyde and secondary amines (under Mannich reaction conditions), aromatic aldehydes and carbon nucleophiles, namely, POCl3/PCl3 and P2S5 has been investigated. The 3-chloropyridazine derivative 13 reacts with hydrazine hydrate to give the 3-hydrazino derivative 14. On treatment with ethyl acetoacetate and/or acetylacetone the hydrazine 14 undergoes cyclization to afford pyrazolone derivative 16 and 3-(3,5-dimethylpyrazol- 1-yl)pyridazine derivative 17, respectively. On reaction with acetylhydrazine in boiling butanol and/or sodium azide in DMF the 3-chloropyridazine derivative 13 affords the triazolo[4,3-b]pyridazine 18 and the tetrazolo[1,5-b]pyridazine 19, respectively. The anti-microbial activity of the synthesized derivatives has been investigated.

scholarly journals Determination of Sodium Azide in Beverages by Ion Chromatography

2000 ◽  
Vol 83 (6) ◽  
pp. 1410-1414 ◽  
Author(s):  
Harumi Oshima ◽  
Eiji Ueno ◽  
Isao Saito ◽  
Hiroshi Matsumoto
Keyword(s):  
Detection Limit ◽  
Sample Preparation ◽  
Sodium Hydroxide ◽  
Ion Chromatography ◽  
Sodium Azide ◽  
Convenient Method ◽  
Sodium Hydroxide Solution ◽  
Hydrazoic Acid ◽  
Suppressed Conductivity Detection

Abstract A convenient method for determination of sodium azide in beverages using ion chromatography is described. This method combines the specificity for azide with a simple sample preparation using a bubble and trap apparatus that removes any interferences. Sodium azide in a sample was acidified, and the azide was converted to the volatile hydrazoic acid, which was trapped in 2.5mM sodium hydroxide solution. Determination was performed by isocratic ion chromatography using suppressed conductivity detection. Calibration curves were linear for 0.5 to 20 μg/mL sodium azide and the detection limit was 0.05 μg/mL. Recoveries of sodium azide from spiked samples (10.0 μg/g) were more than 82.6%. The method was then used to analyze various beverages.

ISOMERIC 5-(SUBSTITUTED)AMINOTHIATRIAZOLE AND 1-SUBSTITUTED-TETRAZOLINETHIONES

1959 ◽  
Vol 37 (1) ◽  
pp. 101-109 ◽  
Author(s):  
Eugene Lieber ◽  
J. Ramachandran
Keyword(s):  
Electrical Properties ◽  
Sodium Azide ◽  
Side Reactions ◽  
Hydrazoic Acid ◽  
Azide Ion ◽  
Rearrangement Mechanism

The reaction of organic isothiocyanates with sodium azide in ethanol and water has been investigated. Water is shown to be the more advantageous solvent for this reaction giving higher yields and initially purer 1-substituted-tetrazoline-5-thiones. A series of these latter compounds was made by this procedure. The yield of product appears to be dependent on the electrical properties of the substituent of the isothiocyanate, the yields decreasing as the electron-donating properties increase. A series of new 4-substituted-thiosemicarbazides has been prepared and converted by diazotization to the corresponding 5-(substituted)aminothiatriazoles. A theory to account for the differences in the mode of reaction of hydrazoic acid and azide ion is presented and discussed. The basic conversion of 5-(substituted)aminothiatriazoles to 1-substituted-tetrazolinethiones may involve a simple dearrangement–rearrangement mechanism complicated by side reactions. A summary of known isomeric 5-(substituted)aminothiatriazoles and 1-substituted-tetrazolinethiones is presented.

scholarly journals Synthesis of Some Heterocyclic Compounds Derived from Furfural

2018 ◽  
Vol 2 (1) ◽  
Keyword(s):  
Sodium Azide ◽  
Ring Opening ◽  
Heterocyclic Compounds ◽  
Pyrimidine Derivative ◽  
Heterocyclic Synthesis ◽  
Pyrimidine Derivatives ◽  
Triazole Derivatives ◽  
The Third

We know that most heterocyclic compounds are drugs or co- drugs. In our investigation furfural was used as a precursor for heterocyclic synthesis, either by ring opening of furfural going to pyrimidine derivative E3 then functionalizing this pyrimidine into its derivatives E8, E10 and cyclization into oxadiazole and thiadiazoles E8, 11. Or the reaction of pyrimidine with dimedon derivatives to afford dimedino pyrimidine derivatives. The second pathway involve the synthesis of oxamyl derivative of pyrmidine E21-25 these compounds were cyclized into new oxadiazoles E24-26. The third pathway involve the synthesis of mucobromic esters E27-29 from MBA acid then these esters were converted into the correspondig lactones E30-32 and E32-36 while reacting MBA with amines affording N-alkyland N-amidolactams. The last pathway was the reaction MBA with methanol, sodium azide to give azidointermeddiate which was cyclized with alkene or alkynes into triazole derivatives E42-49. The synthesized compounds were characterized by IR and some 1 HNMR measurements.

Sign in / Sign up

Export Citation Format

Share Document