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.

scholarly journals Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Hassan Kabirifard ◽  
Pardis Hafez Taghva ◽  
Hossein Teimouri ◽  
Niloofar Koosheshi ◽  
Parastoo Javadpour ◽  
...  
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Organic Ligands ◽  
Carboxyl Group ◽  
Primary Aromatic Amines

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

scholarly journals Room-Temperature, Base-Mediated Selective Synthesis of 2-(Arylamino)ethanols and 2-Aryloxyethanols

SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 124-137 ◽  
Author(s):  
Rahul B. Sonawane ◽  
Swapnali R. Sonawane ◽  
Nishant K. Rasal ◽  
Sangeeta V. Jagtap
Keyword(s):  
Functional Groups ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Alkyl Halide ◽  
Selective Synthesis ◽  
Formal Synthesis ◽  
Mild Conditions ◽  
Primary Aromatic Amines

A simple and efficient protocol for base-mediated selective synthesis of 2-(arylamino)ethanols from primary aromatic amines and 2-aryloxyethanols from phenols, promoted by K2CO3 has been achieved under mild conditions. Even in presence of excess alkyl halide, selective mono-N-alkylation has been achieved. Tolerance of a variety of functional groups is demonstrated by 15 examples of selective N-alkylation of aromatic amines and 19 examples of O-alkylation of phenols. The efficacy of the protocol is demonstrated by the formal synthesis of Ticlopidine­®, Vildagliptin®, Quetiapine®, and Gemfibrozil®.

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).

A Convenient One-Pot Synthesis of Pyrazolo[3,4-d]pyrimidines and s-Triazolo[3,4-b][1,3,5]thiadiazines

1997 ◽  
Vol 52 (11) ◽  
pp. 1401-1412 ◽  
Author(s):  
Zeinab A. Hozien ◽  
Abd El-Wareth A. O. Sarhan ◽  
Hassan A. H. El-Sherief ◽  
Abdalla M. Mahmoud
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Good Yield ◽  
Room Temperature ◽  
Secondary Amines ◽  
One Pot ◽  
Aminomethyl Derivatives ◽  
Primary Aromatic Amines ◽  
The Mannich Reaction ◽  
Primary Aliphatic Amines

Abstract The reaction of 5-amino-3-aryl-1-phenylpyrazoles (1a-d) with formaldehyde and secondary amines in boiling ethanol gave the corresponding 4-alkylaminomethyl derivatives (2a-f) and bis-(4-pyrazolyl)methane (4a,b) as byproduct. Such reaction with primary aliphatic and aro­ matic amines at room temperature afforded 1,3,5-trisubstituted (5a-h) and 1,3.5,7-tetrasubstituted tetrahydropyrazolo[3,4-d]pyrimidines (8a-k) respectively in good yield. Similarily, the Mannich reaction of 5-mercapto-3-phenyl-1,2,4-triazole (9) with secondary amines, in boiling ethanol, and primary aromatic amines, at room temperature, gave 2 -substituted aminomethyl derivatives (10a-c) and (14a-g) respectively,while with primary aliphatic amines, p-toluidine and p-anisidine,at room temperature,and with other primary aromatic amines, in boiling ethanol, afforded the cyclized products 12,4-triazolo[3,4-b]thiadiazines (13a-e); (15f,g) and (15a-e), respectively.

Rearrangements in the Furan Series. II. The Reaction Between Furfuraldehyde and Aromatic Amines

1979 ◽  
Vol 32 (5) ◽  
pp. 1079 ◽  
Author(s):  
KG Lewis ◽  
CE Mulquiney
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Room Temperature ◽  
Furan Series ◽  
Mineral Acids ◽  
Primary Aromatic Amines ◽  
Stable Structures

A survey of the reaction of a variety of primary aromatic amines with furfuraldehyde has shown that, in most cases, the product isolated has the 2,4-diarylaminocyclopent-2-enone structure as established in the case of aniline. In a number of cases the products were shown to be the isomeric 4,5-diarylamino derivatives. It has been established that the 2,4-diarylamino derivatives are the more stable structures and that 4,5-disubstituted isomers are intermediates. Treatment of the 4,5-diarylaminocyclopent-2-enones with mineral acids gives a facile ring opening at room temperature to form the corresponding Stenhouse salt. A mechanism is suggested for both the above reactions. The results of some previous work are clarified.

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.

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