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).

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 Regioselective convergent synthesis of 2-arylidene thiazolo[3,2-a]pyrimidines as potential anti-chikungunya agents

RSC Advances ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 5191-5195 ◽  
Author(s):  
Mohamed Fares ◽  
Patrick M. McCosker ◽  
Muhammad A. Alsherbiny ◽  
Anthony C. Willis ◽  
Timothy Clark ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Sodium Acetate ◽  
Anhydrous Sodium Acetate ◽  
Regioselective Synthesis ◽  
One Pot ◽  
Bromoacetic Acid ◽  
Convergent Synthesis ◽  
The One

Convergent and convenient regioselective synthesis of novel thiazolo[2,3-a]pyrimidines was accomplished using the one-pot reaction of 6-ethylthiouracil, bromoacetic acid, anhydrous sodium acetate, acetic anhydride, acetic acid and suitable aldehyde.

Synthesis of 2-Aryl-4-arylazo-2-thiazolin-5-ones and their reaction with aromatic amines

1976 ◽  
Vol 29 (7) ◽  
pp. 1627 ◽  
Author(s):  
AM Khalil ◽  
IIA El-Gawad ◽  
HM Hassan
Keyword(s):  
Acetic Acid ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Diazonium Salt ◽  
Coupling Reaction ◽  
Catalytic Amount ◽  
Heterocyclic Ring ◽  
Primary Aromatic Amines

2-Aryl-4-arylazo-2-thiazolin-5-ones are prepared by a coupling reaction between thioaroylglycine and the appropriate diazonium salt. Their heterocyclic ring is readily opened by the action of primary aromatic amines in acetic acid containing a catalytic amount of sodium acetate with the formation of 1,5,Nx-triaryl-1H-l,2,4-triazole-3-carboxamides.

Reaction of 2-Aryl-4-arylmethylene-2-oxazolin-5-ones with amines

1973 ◽  
Vol 26 (4) ◽  
pp. 827 ◽  
Author(s):  
AM Islam ◽  
AM Khalil ◽  
El-Gawad II Abd
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

1,2-Diaryl-4-arylmethylene-2-imidazolin-5-ones were prepared by the interaction of primary aromatic amines with 2-aryl-4-arylmethylene-2- oxazolin-5-ones in the presence of acetic acid and sodium acetate. The same imidazolones were also obtained by the cyclization of the arylamides of α-arylamido-β-arylacrylic acids under the same reaction conditions. A possible reaction mechanism was postulated.

Reaction of 2-(m-Tolyl)-4-arylmethylene-2-oxarolin-5-ones with amines

1973 ◽  
Vol 26 (8) ◽  
pp. 1701 ◽  
Author(s):  
AM Islam ◽  
AM Khalil ◽  
MS El-Houseni
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Direct Interaction ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
Facile Route

A facile route for the preparation of 1,2-diaryl-4-arylmethylene-2-imidazolin-5-ones was established by the direct interaction of primary aromatic amines with 2-(m-tolyl)-4-arylmethylene-2-oxazolin-5-ones in acetic acid containing catalytic amounts of sodium acetate. The same imidazolones were also obtained by cyclization of the aryl- carboxamides of α-arylcarboxamido-β-arylacrylic acids under the same reaction conditions. A possible reaction mechanism was discussed.

The action of arylamines on some substituted 2-Thiazolin-5-ones

1974 ◽  
Vol 27 (9) ◽  
pp. 2035 ◽  
Author(s):  
AM Khalil ◽  
El-Gawad II Abd ◽  
M Hammouda
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Heterocyclic Ring ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

The heterocyclic ring in 2-aryl-4-arylmethylene- and 4-arylmethylene-2-benzylthio-2-thiazolin-5-ones is readily opened by the action of primary aromatic amines in acetic acid containing a catalyticamount of sodium acetate with the formation of 1,2-diaryl-4-arylmethylene-2-imidazolin-5-ones and of 3-aryl-5-arylmethylene-2-thiohydantoins respectively. 4-Benzylidene-1-(p-chloropheny1)-2-phenyl-2-imidazolin-5-one was also obtained by the cyclization of the anilide of α-(p-chlorothiobenzamido)-β-phenylacrylic acid under the same reaction conditions. A possible reaction mechanism is postulated.

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.

The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1623-1632 ◽  
Author(s):  
Elina Marinho ◽  
M. Proença
Keyword(s):  
Acetic Acid ◽  
Trifluoroacetic Acid ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Ethyl Chloroformate ◽  
Convenient Synthesis ◽  
Primary Aromatic Amines

2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

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