Aliphatic and aromatic 5-nitro-2-furylamines and aromatic 5-nitrofurfuryl ethers

1983 ◽  
Vol 48 (9) ◽  
pp. 2682-2692 ◽  
Author(s):  
Raul Mocelo ◽  
Jaroslav Kováč
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Secondary Amines ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

Tertiary 5-nitrofurylamines were prepared by a nucleophilic substitution of 5-nitro-2-furfuryl bromide (I) with aliphatic secondary amines. According to reaction conditions N-(5-nitro-2-furfuryl)-X-phenylamines or their mixture with N,N-di(5-nitro-2-furfuryl)-X-phenylamines were obtained from the reaction of I with substituted primary aromatic amines. Compound I gave with 2-aminophenol a mixture of O- and N-mono- and disubstituted derivatives, and with ethyl salicylate ethyl 2-(5-nitro-2-furfuryloxy)benzoate.

Preparation of aromatic amines by copper-catalyzed coupling of boronic acids with aqueous ammonia

2010 ◽  
Vol 88 (9) ◽  
pp. 964-968 ◽  
Author(s):  
Zhaoqiong Jiang ◽  
Zhiqing Wu ◽  
Lixia Wang ◽  
Di Wu ◽  
Xiangge Zhou
Keyword(s):  
Aromatic Amines ◽  
Aqueous Ammonia ◽  
Environmentally Friendly ◽  
Boronic Acids ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Primary Aromatic Amines

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.

scholarly journals Efficient N-formylation of primary aromatic amines using novel solid acid magnetic nanocatalyst

RSC Advances ◽  
2020 ◽  
Vol 10 (67) ◽  
pp. 41229-41236
Author(s):  
Jitendra Kumar Yadav ◽  
Priyanka Yadav ◽  
Satish K. Awasthi ◽  
Alka Agarwal
Keyword(s):  
Magnetic Nanoparticles ◽  
Aromatic Amines ◽  
Sulfonic Acid ◽  
Solid Acid ◽  
Recyclable Catalyst ◽  
Primary Amines ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
First Time

Sulfonic acid functionalized over biguanidine fabricated silica-coated heterogeneous magnetic nanoparticles (NP@SO3H) have been synthesized, well characterized and explored for the first time, as an efficient and recyclable catalyst for N-formylation of primary amines under mild reaction conditions.

Studies on Synthesis of Some Novel Thioureides of 2-(4-Methyl-phenoxymethyl)benzoic Acid with Antimicrobial Activity

2008 ◽  
Vol 59 (10) ◽  
Author(s):  
Carmen Limban ◽  
Alexandru-Vasile Missir ◽  
Ileana Cornelia Chirita ◽  
Corina Ilie ◽  
Miron Teodor Caproiu
Keyword(s):  
Antimicrobial Activity ◽  
Benzoic Acid ◽  
Acid Chloride ◽  
Thionyl Chloride ◽  
Aromatic Amines ◽  
Ammonium Thiocyanate ◽  
Spectral Studies ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
Benzoyl Isothiocyanate

Thioureides of 2-(4-methyl-phenoxymethyl)benzoic acid have been synthesised by reaction of 2-(4-methyl-phenoxymethyl)benzoyl isothiocyanate with primary aromatic amines. The mentionated isothiocyanate was obtained in the reaction of the 2-(4-methyl-phenoxymethyl)benzoic acid chloride with ammonium thiocyanate. The acid chloride was prepared by reacting the coresponding acid, the 2-(4-methyl-phenoxymethyl)benzoic acid, with thionyl chloride and the aforementioned acid from potassium para-cresolate with phtalide. The reaction conditions were established to ensure the best yields. These new thioureides have been characterized by means of elemental analysis, IR and NMR spectral studies.

Cu-Catalyzed Allylation of Amines with Cyclopropyldiphenylsulfonium Trifluoromethanesulfonate

Synthesis ◽  
2022 ◽  
Author(s):  
Yu Ma ◽  
Ze-Yu Tian ◽  
Shuang-Yang Zheng ◽  
Cheng-Pan Zhang
Keyword(s):  
Aromatic Amines ◽  
Functional Group ◽  
Secondary Amines ◽  
Reaction Conditions ◽  
Drug Molecules ◽  
Wide Range ◽  
Catalyzed Reactions ◽  
Cyclic Compounds

Cyclopropyldiphenylsulfonium salt is a famous ylide precursor that was previously extensively employed in the preparation of cyclic compounds and has been successfully utilized as an efficient allylation reagent in this work. The Cu-catalyzed reactions of cyclopropyldiphenylsulfonium trifluoromethanesulfonate with amines in the presence of an appropriate ligand provided the N-allylated products in good yields. Aliphatic/aromatic amines and primary/secondary amines were all mildly converted under the reaction conditions. This protocol was also applicable to N-functionalization of drug molecules, supplying the corresponding N-allylated compounds in satisfactory yields. The reaction showed good functional group tolerance, a wide range of substrates, and excellent chemoselectivity, which offered an interesting method for the synthesis of N-allyl amines.

Green H2O-Promoted Solvent-Free Synthesis of Enaminocarbonyl Compounds with High Stereoselectivity from Electron-Deficient Terminal Alkynes

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 878-882
Author(s):  
Xiao Yun Chen ◽  
Luming Zhang ◽  
Yaonan Tang ◽  
Shuxia Yuan ◽  
Baocheng Zhu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Aromatic Amines ◽  
Solvent Free ◽  
Secondary Amines ◽  
Terminal Alkynes ◽  
Primary Aromatic Amines ◽  
Solvent Free Synthesis ◽  
High Stereoselectivity

A green H2O-promoted solvent-free hydroamination of electron-deficient terminal alkynes with amines has been developed. All secondary amines, including aliphatic and aromatic amines, gave the corresponding (E)-enamines in good to excellent yields, whereas primary aromatic amines afforded Z-configured products in moderate yields. Propiolates, propyn-1-ones, propynamides, and 1-(ethynylsulfonyl)-4-methylbenzene were explored in this Michael addition.

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.

Synthesis of 1,3-diazaspiro[5,5]undecanes and 1-thia-3-azaspiro[5,5]undec-2-enes by reaction of 2-cyanocyclohexylideneacetyl isothiocyanate with amines and sodium hydrogen sulfide

1987 ◽  
Vol 52 (4) ◽  
pp. 989-994 ◽  
Author(s):  
Milan Dzurilla ◽  
Ondrej Forgáč ◽  
Peter Kutschy ◽  
Pavol Kristian ◽  
Dušan Koščík ◽  
...  
Keyword(s):  
Hydrogen Sulfide ◽  
Alkaline Medium ◽  
Mass Spectroscopy ◽  
Aromatic Amines ◽  
Secondary Amines ◽  
H Nmr ◽  
Sodium Hydrogen ◽  
Elemental Analyses ◽  
Primary Aromatic Amines ◽  
C Nmr

2-Cyanocyclohexylideneacetyl isothiocyanate (II) reacts with sodium hydrogen sulfide to give 1-thia-3-azaspiro[5,5]undecane. Reaction of II with secondary amines afforded 1-thia-3-azaspiro[5,5]undec-2-enes whereas primary aromatic amines gave 1,3-diazaspiro[5,5]undecanes under the same conditions. Both types of reactions proceed via substituted thioureas which were isolated pure only in the case of 4-methylaniline and 4-methoxyaniline. They were cyclized in alkaline medium to the corresponding diazaspiro derivatives. The structure of the synthesized compounds was confirmed by their elemental analyses and IR, 1H NMR, 13C NMR and mass spectroscopy.

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.

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