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.

The Synthesis and Characterization of some New Thioureides of 2-(4-Methyl-phenoxymethyl)benzoic Acid with Antimicrobial Activity

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Carmen Limban ◽  
Alexandru-Vasile Missir ◽  
Ileana Cornelia Chirita ◽  
George Mihai Nitulescu1 ◽  
Corina Ilie ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Benzoic Acid ◽  
Acid Chloride ◽  
Ammonium Thiocyanate ◽  
Antimicrobial Activities ◽  
Synthesis And Characterization ◽  
Primary Aromatic Amines ◽  
Benzoyl Isothiocyanate ◽  
New Compounds

It is well known that many compounds bearing thioureide structure have been reported to have antimicrobial activity and some of these thioureide compounds are found to be associated with other therapeutical activities. The present application is a continuation of our research concerning the synthesis and characterization of 2-(4-methyl-phenoxymethyl)benzoic acid thioureides with antimicrobial activities. The new thioureides were obtained in three stages. In the first stage we prepared the 2-(4-methyl-phenoxymethyl)benzoic acid by reacting potassium para-cresolate with phtalide. The second stage consists in the synthesis of the 2-(4-methyl-phenoxymethyl)benzoic acid chloride and, in the third phase, the acid chloride aforementioned is refluxed with ammonium thiocyanate the resulting 2-(4-methyl-phenoxymethyl)benzoyl isothiocyanate being treated with primary aromatic amines to obtain the new compunds. We established the optimal reaction conditions for the new compounds synthesizing process of with high purity and yields. The new compounds, which are not mentioned in the literature concerning this domain, have been characterized by their physical properties (melting point, solubility) and the structures were confirmed by elemental analysis, 1H-NMR, 13C-NMR and IR spectral methods.

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.

Orthoamide und Iminiumsalze, LXXXVIII. Synthese N,N,N′,N′,N″,N″-persubstituierter Guanidiniumsalze aus N,N′-persubstituierten Harnstoff/Säurechlorid-Addukten**

2015 ◽  
Vol 70 (1) ◽  
pp. 9-27
Author(s):  
Willi Kantlehner ◽  
Ralf Kreß ◽  
Jochen Mezger ◽  
Georg Ziegler
Keyword(s):  
Methyl Iodide ◽  
Thionyl Chloride ◽  
Aromatic Amines ◽  
Phosphorus Pentachloride ◽  
Phosphoryl Chloride ◽  
Primary Aromatic Amines ◽  
Guanidinium Salt

AbstractN,N,N′,N′,N″,N″-Hexamethylguanidinium chloride9cwas prepared by treating the reaction mixture formed fromN,N,N′,N′-tetramethylurea (1a) and phthaloyl chloride (16) with dimethyltrimethylsilylamine15.N,N,N′,N′-Tetramethyl-chloroformamidinium chloride (2a) is an intermediate in this synthesis. The chloroformamidinium chloride2acan also be prepared by treating the urea1awith thionyl chloride or phosphorus pentachloride, respectively. The guanidinium salt9ccan be obtained from the crude2athus prepared and the silylamine15. From urea/phosphoryl chloride adducts and primary aromatic amines have been prepared guanidines38, which are converted toN,N′-diaryl-N,N′,N″,N″-tetramethyl-guanidinium iodides39on treatment with methyl iodide. TheN,N′,N″-trimethyl-N,N′,N″-triphenylguanidinium salt44awas prepared from the chloroformamidinium salt43andN-methylaniline. The guanidinium salt9cis the reaction product when the urea1a/POCl3adduct is treated with the silylamine15.

scholarly journals Synthesis of certain pyrrole derivatives as antimicro-bial agents

2009 ◽  
Vol 59 (2) ◽  
pp. 145-158 ◽  
Author(s):  
Mosaad Mohamed ◽  
Ramdan El-Domany ◽  
Rania Abd El-Hameed
Keyword(s):  
Antimicrobial Activity ◽  
Aromatic Amines ◽  
Gram Negative Bacteria ◽  
Gram Positive ◽  
Pyrrole Derivatives ◽  
Gram Negative ◽  
Primary Aromatic Amines ◽  
Aryl Amines ◽  
Bacteria And Fungi

Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds was carried out against Gram-positive, Gram-negative bacteria and fungi. Some of the prepared compounds, [2-amino-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrole-3-carbonitriles (1b), 2-amino-3-carbamoyl-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrroles (2b),N-(3-cyano-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3b),N-(3-cyano-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3c), 2-amino-1-(4-methoxyphenyl)-4,5-diphenyl-3-tetrazolo-1H-pyrroles (5d),7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-ones (7d), 7-(3-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione (9b) andN-(7-(2-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine)-N-aryl amines (10a)] showed potent antimicrobial activity.

scholarly journals Synthesis, Characterizations and Antimicrobial Activity of Metal Complexes of 2-(2-Furanylmethylaminocarbonyl)benzoic Acid

2011 ◽  
Vol 8 (1) ◽  
pp. 443-448 ◽  
Author(s):  
R. H. Patel ◽  
B. L. Hiran
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Transition Metal ◽  
Benzoic Acid ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Elemental Analysis ◽  
Magnetic Moments ◽  
Thermal Studies ◽  
Spectral Studies

The ligand, 2-(2-furanylmethylaminocarbonyl)benzoic acid (FMBA) and it’s transition metal complexes have been synthesized and characterized by elemental analysis, spectral studies, magnetic moments and thermal studies. The antifungal activity of all the samples was monitored against common fungi.

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.

scholarly journals Synthesis, Characterization and Antimicrobial Activity of Ni(II), Zn(II), and Cd(II) Complexes of 3/4-Bromo-Benzoic Acid (Phenyl-Pyridine-2-yl-Methylene)-Hydrazide Ligand

2020 ◽  
Vol 9 (4) ◽  
pp. 1529-1537
Keyword(s):  
Antimicrobial Activity ◽  
Benzoic Acid ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Metal Ion ◽  
Trichophyton Rubrum ◽  
Salmonella Typhi ◽  
Spectral Studies ◽  
Mass Analysis ◽  
Uv Visible

New transition metal complexes [Ni(L)2], [Zn(L)Cl], [Zn(L)2] and [Cd(L)2] were synthesized from 3-bromo-benzoic acid (phenyl-pyridin-2-yl-methylene)-hydrazide (3Bbpph) and 4-bromo-benzoic acid (phenyl-pyridin-2-yl-methylene)-hydrazide (4Bbpph) ligands and were characterized by different physicochemical and spectral studies - IR, elemental, UV Visible, 1H NMR spectra and mass analysis. The data revealed the presence of tetra-coordinate [Zn (L)Cl], whereas [Ni(L)2], [Zn(L)2], and [Cd(L)2] complexes consist of metal ion coordinated with two molecules of ligand to form octahedral geometry. The ligands act as monobasic, tridentate, and coordinated through enolate-O, azomethine-N, and pyridyl-N atoms. The antimicrobial activity of the ligands and metal complexes was investigated against Staphylococcus Aureus, Streptococcus Pyogenes, Escherichia coli, Salmonella typhi, Candida Albicans and Trichophyton Rubrum which revealed that the metal complexes exhibit greater activity than the parent ligands.

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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