scholarly journals Reactions of 4-hydroxycoumarin with heterocyclic aldehydes

2021 ◽  
Vol 9 (3) ◽  
Author(s):  
Renáta Gašparová ◽  
Katarína Kotlebová ◽  
Margita Lácová
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Microwave Irradiation ◽  
Sodium Hydroxide ◽  
Acid Medium ◽  
Sodium Acetate ◽  
Toluenesulfonic Acid ◽  
Heterocyclic Aldehydes

Reactions of 4-hydroxycoumarin 1 with heterocyclic aldehydes 2-4 led to bis-4-hydroxycoumarin derivatives 5-7 under microwave irradiation as well as under the classical heating. The subsequent reactions of products 5-7 are described. 4,4’-Epoxydicoumarins 8, 9 were prepared by the reaction of 5-7 in acetic acid / p-toluenesulfonic acid medium. Compound 10 was prepared by the reaction of 5 in acetic anhydride in the presence sodium acetate. Dioxocine-1,15-dione 11 was prepared by the reaction of 6 with dichloromethane in sodium hydroxide-toluene.

Microwave Irradiated Acetylation of p-Anisidine: A Step towards Green Chemistry

2008 ◽  
Vol 6 (1) ◽  
Author(s):  
Mousumi Chakraborty ◽  
Vaishali Umrigar ◽  
Parimal A. Parikh
Keyword(s):  
Acetic Acid ◽  
Reaction Time ◽  
Green Chemistry ◽  
Acetic Anhydride ◽  
Microwave Irradiation ◽  
Organic Solvent ◽  
Reaction Times ◽  
Microwave Energy ◽  
Operating Parameters ◽  
Feed Composition

The present study aims at assessing the effect of microwave irradiation against thermal heat on the production of N-acetyl-p-anisidine by acetylation of p-anisidine. The acetylation of p-anisidine under microwave irradiation produces N-acetyl-p-anisidine in shorter reaction times, which offers a benefit to the laboratories as well as industries. It also eliminates the use of excess solvent. Effects of operating parameters such as reaction time, feed composition, and microwave energy and reaction temperature on selectivity to the desired product have been investigated. The results indicate as high as a 98% conversion of N-acetyl-p-anisidine can be achieved within 12-15 minutes using acetic acid. The use of acetic acid as an acetylating agent against conventionally used acetic anhydride eliminates the handling of explosive acetic anhydride and also the energy intensive distillation step for separation of acetic acid. Organic solvent like acetic anhydride are not only hazardous to the environment, they are also expensive and flammable.

THE PREPARATION OF 9-HYDROXYPYRAZOLO[3,4-b]QUINOLINES

1966 ◽  
Vol 44 (17) ◽  
pp. 2009-2014 ◽  
Author(s):  
R. T. Coutts ◽  
J. B. Edwards
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Sodium Borohydride ◽  
Sodium Acetate ◽  
The Other ◽  
Reduction Product ◽  
Type I

4-(2-Nitrobenzylidene)-2-pyrazolin-5-ones (I) were best prepared by heating o-nitrobenzaldehyde and 2-pyrazolin-5-ones in acetic anhydride containing fused sodium acetate (cf. Erlenmeyer azlactone synthesis). Pyrazolones of type I were reductively cyclized with cyclohexene and palladium–charcoal, and gave 3a,4,9,9a-tetrahydro-9-hydroxy-1H-pyrazolo-[3,4-b]quinolines (II) which, as expected, were amphoteric compounds. Of the three other methods of reduction used in this study, two (zinc and acetic acid; sodium borohydride and palladium–charcoal) were capable of producing pyrazoloquinolines, but were less reliable. The other method employed (hydrazine hydrate and palladium–charcoal) caused degradation of the pyrazolone molecule in the two cases examined, and in both, bis(2-aminobenzylidene) hydrazine (V) was the reduction product isolated.

An efficient synthesis of pterosin C and other pterosins

1984 ◽  
Vol 62 (10) ◽  
pp. 1945-1953 ◽  
Author(s):  
Kam-Mui Eva Ng ◽  
Trevor C. McMorris
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Methyl Ether ◽  
Sodium Acetate ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans

A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

2010 ◽  
Vol 65 (12) ◽  
pp. 1509-1515 ◽  
Author(s):  
Manjunatha Kumsi ◽  
Boja Poojary ◽  
Prajwal Lourdes Lobo ◽  
Nalilu Suchetha Kumari ◽  
Anoop Chullikana
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
One Pot ◽  
Biological Studies ◽  
Elemental Analyses

The key precursor rac-2-(4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/ substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

scholarly journals Treating kraft mill extract using bipolar membrane electrodialysis for the production of acetic acid

TAPPI Journal ◽  
2016 ◽  
Vol 15 (3) ◽  
pp. 215-226 ◽  
Author(s):  
RAVIKAT PATIL ◽  
JOSEPH GENCO ◽  
HEMANT PENDSE ◽  
ADRIAAN VAN HEININGEN
Keyword(s):  
Acetic Acid ◽  
Energy Consumption ◽  
Sodium Hydroxide ◽  
Current Density ◽  
Salt Solution ◽  
Sodium Acetate ◽  
Process Conditions ◽  
Sodium Acetate Solution ◽  
Bipolar Membrane ◽  
Bipolar Membrane Electrodialysis

The objective of this work was to determine the process conditions for converting sodium acetate, the major component of alkaline hardwood extract, into acetic acid and sodium hydroxide using bipolar membrane electrodialysis (BPMED). The effects of current density and sodium acetate concentration in the feed-salt solution were evaluated using synthetic sodium acetate solution in a feed and bleed mode. This mode of operation represents semibatch processing and was useful for determining the current efficiencies, energy consumption, and other system parameters for the production of about 160 g/L of acetic acid; maximum achievable concentration of acetic acid in electrodialysis; and 30 g/L of sodium hydroxide, which is the concentration sufficient for the extraction of sodium acetate from hardwood. The feed and bleed mode experiments performed at 60 mA/cm2 using 130 and 85 g/L sodium acetate as feed-salt solutions produced similar results, except for a small change in the amount of water transported into the acid and base compartments. The feed and bleed mode experiment performed at low current density of 40 mA/cm2 using 50 g/L sodium acetate as feed-salt solution produced almost similar quantities of acetic acid and sodium hydroxide as those in the other feed and bleed mode experiments. However, the energy consumption and current efficiencies were lower than those for the experiments performed at the current density of 60 mA/cm2.

Fluorine-containing Heterocycles: Part II Synthesis and Reactions of New Thieno[2,3-b]Pyridine Derivatives Bearing Trifluoromethyl Group

2005 ◽  
Vol 2005 (7) ◽  
pp. 461-468 ◽  
Author(s):  
Abdu E. Abdel-Rahman ◽  
Etify A. Bakhite ◽  
Elham A. Al-Taifi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Triethyl Orthoformate ◽  
Trifluoromethyl Group ◽  
Pyridine Derivatives ◽  
Unexpected Product ◽  
Acyl Azide ◽  
Hydrolysis Of ◽  
Heterocyclic Aldehydes

Ethyl [3-cyano-6-(2-thienyl)-4-trifluoromethylpyridin-2-ylthio]acetate (2) and ethyl 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylate (3) were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with ethyl chloroacetate. The reaction of both 2 and 3 with hydrazine hydrate under different conditions was studied. The main products were [3-cyano-6-(2-thienyl)-4-trifluoromethyl-2-pyridinylthio]acetohydrazide (4) and 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carbohydrazide (5). The condensation of acethydrazide 4 with some aromatic or heterocyclic aldehydes yielded the corresponding hydrazones 6a–d which underwent intramolecular Thorpe–Ziegler cyclisation to give the N1-aryl or heteroaryl-methylene-3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carbohydrazides (7a–d). Treatment of 7a–d with triethyl orthoformate led to the formation of pyridothienopyrimidine derivatives 8a–d. Heating carbohydrazide 5 with acetic acid gave an unexpected product which was assigned as 3-amino-2-methyl-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine-4(3H)-one (12). Moreover, the reaction of 5 with other reagents such as acetic anhydride, formic acid, acetylacetone and/or triethyl orthoformate were carried out and their products were identified. Diazotisation of 5 produced the corresponding acyl azide 18 which underwent Curtius rearrangement to furnish the imidazolone derivative 20. Hydrolysis of the ester 3 gave the aminoacid 21 which in turn was converted into the oxazinone derivatives 22 and 23. Recyclisation of 22 and 23 into some pyrimidinone derivatives (12 and 24–26) was carried out.

Cyclisation of 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoins

1981 ◽  
Vol 36 (4) ◽  
pp. 501-504 ◽  
Author(s):  
A. F. A. Shalaby ◽  
M. A. Abdel Aziz ◽  
S. S. M. Boghdadi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Anhydrous Sodium Acetate ◽  
Primary Aromatic Amines ◽  
Hydantoin Derivatives

Abstract 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoin derivatives (3a-f) were cyclised with acetic anhydride to give the bicyclic products (4a-f). Compounds 4 a, b condensed with aromatic aldehydes in acetic acid and in presence of anhydrous sodium acetate yielding the corresponding arylidene derivatives (5a-c). Compounds 4a, b also couple with aryldiazonium salts to give the expected coloured arylazo compounds (6a-j). 4 a, b reacted with formaldehyde and primary aromatic amines in ethanol to give the corresponding Mannich bases (7a-f).

scholarly journals Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-Ones and 1,2,4-Triazin-6(5H)-Ones Classes

2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Sodium Acetate ◽  
Artemia Salina ◽  
Ft Ir ◽  
New Compounds ◽  
Acetic Acids

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.

scholarly journals Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-Ones and 1,2,4-Triazin-6(5H)-Ones Classes

2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Sodium Acetate ◽  
Artemia Salina ◽  
Ft Ir ◽  
New Compounds ◽  
Acetic Acids

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.

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