Reaction Of O-phenylenediamine Research Articles

Water-Accelerated Selective Synthesis of 1,2-Disubstituted Benzimidazoles at Room Temperature Catalyzed by Brønsted Acidic Ionic Liquid

An environmentally benign method for the rapid and selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles by the reaction of o-phenylenediamines and aromatic aldehydes in the presence of 1-methylimidazolium triflouroacetate ([Hmim]TFA) at room temperature under aqueous conditions is described. The ionic liquid is reusable and could be recycled for several runs without any decrease in its efficiency.

Two directions of reaction between aminothiophenol and 3-bromoarylmaleimides

O V Lately a report was published on the reaction of ophenylenediamine with N-arylmaleimides [1] leading through the recyclization of the latter to substituted quinazolinones. We attempted to bring into similar reaction the o-aminothiophenol and 3-bromomaleimide. It was expected that the reaction of aminothiophenol (I) with 3-bromomaleimide II through the stage of S-alkylation followed by recyclization of intermediate III would provide N-phenyl-2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-ylidene)acetamide (IV) (see the Scheme). It was established however that in reaction performed in ethanol and other solvents acetamide IV was the minor product, and the major product unexpectedly proved to be 2-phenyl-1,2,3,9-tetrahydrobenzo[b]pyrrolo[1,4]thiazine-1,3-dione (V) formerly obtained [2] in the reaction of aminothiophenol and 3,4-dibromomaleimide. The formation of this product apparently occurred by the alternative transformation of the intermediate, 3-(2-aminophenylsulfanyl)-1-phenyl-2,5-dihydro-1H-pyrrole-2,5dione (III), through the stages of amino group addition to an activated double bond by the Michael type reaction with the subsequent oxidation of compound VI, 2-phenyl1,2,3,3a,9,9a-hexahydrobenzo[b]pyrrolo[3,4-e][1,4]thiazine-1,3-dione. N1-Phenyl-2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-ylidene)acetamide (IV) and 2-phenyl1,2,3,9-tetrahydrobenzo[b]pyrrolo[3,4-e][1,4]thiazine-1,3-dione (V). Equimolar quantities (0.01 mol each) of phenylmaleimide and 2-aminothiophenol were heated in ethanol for 1–2 h. The precipitate was separated,

M(HSO4)n-Promoted Synthesis of 2-Aryl-1-arylmethyl-1H-1,3-benzimidazole Derivatives

We have developed a highly selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles from the reaction of o-phenylenediamines and aromatic aldehydes in the presence of metal hydrogen sulfates [M(HSO4)n] in water and also under solvent-free conditions in good to excellent yields.

3,3′-Dimethoxy-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenol

The title Schiff base compound, C19H20N2O4, was synthesized by the reaction of o-phenylenediamine with 6-methoxysalicylaldehyde. The central benzene ring makes dihedral angles of 2.78 (5) and 73.98 (5)° with the two terminal phenol rings. Each methoxy group is coplanar with the attached phenol ring. The crystal structure is stabilized by intramolecular O—H...N and intermolecular C—H...O hydrogen bonds.

Synthesis and physico-chemical studies on complexes of 1,2-diaminophenyl- N, N′-bis-(2-pyridinecarboxaldimine), ( L): A spectroscopic approach on binding studies of DNA with the copper complex

The Schiff base ligand, 1,2-diaminophenyl- N, N′-bis-(2-pyridinecarboxaldimine), ( L) has been synthesized by the reaction of o-phenylenediamine and 2-pyridinecarboxaldehyde, and a series of mononuclear complexes of the type [ML(NO 3) 2] [M = Co(II), Ni(II), Cu(II) and Zn(II)] has also been synthesized. The formation of the Schiff base ligand ( L) and its complexes have been envisaged from IR, 1H and 13C NMR studies. The absorption band observed in the electronic spectra and magnetic moment values confirm an octahedral environment around the metal ion. The molar conductivity measurements confirm the non-ionic character of these complexes. Fluorescence and UV–Vis absorption studies performed on the Cu(II) complex revealed a significant binding ability to DNA.

Synthesis of 2-mercaptobenzimidazole from the reaction of o-phenylene diamine and carbon disulfide in the presence of potassium hydroxide

The reaction of o-phenylene diamine and carbon disulfide to synthesize 2-mercaptobenzimidazole (MBI) enhanced by potassium hydroxide was carried out in a homogeneous solution. No catalysts are required in the reaction. In addition to the reaction of carbon disulfide and hydrogen sulfide to produce S 2− and CS 3 2−, potassium hydroxide is also acted as the enhancer to promote the reaction of synthesizing MBI. A mixture of organic solvent (protic or aprotic solvent) and water is used as the reaction solution in order to obtain a homogeneous phase. The effects of the reaction conditions, including the amount of o-phenylene diamine, amount of carbon disulfide, organic solvents, volume ratio of organic solvent to water, and temperature, on the conversion of o-phenylene diamine were investigated in detail. An appropriate amount of KOH is recommended to produce a high yield of MBI and a high reaction rate in using protic solvent/water as the mixed solution. Nevertheless, the conversion is increased with the increase in the amount of KOH using aprotic solvent. This behavior is different from that of the KOH effect on the conversion of o-phenylene diamine using protic solvent/water as the mixed solution.

Chemiluminescent imaging analysis of interferon alpha in serum samples

Enzyme-linked immunosorbent assay (ELISA), horseradish peroxidase (HRP)-catalyzed fluorescent reaction, and oxalate chemiluminescence imaging analysis have been combined to develop a sensitive, simple, and rapid method for analysis of interferon alpha (alpha-IFN) in human serum samples. A typical "sandwich type" immunoassay was used. Reaction of o-phenylenediamine (OPD) with hydrogen peroxide (H(2)O(2)), catalyzed by HRP, produced 2,3-diaminophenazine (PDA), which was detected by chemiluminescence imaging analysis with the bis(2,4,6-trichlorophenyl)oxalate (TCPO)-H(2)O(2)-glyoxaline-PDA chemiluminescent system. The TCPO chemiluminescent imaging system is more sensitive and the chemiluminescence quantum yield is at least five times higher than for the luminol-H(2)O(2)-HRP-PIP (p-iodophenol) chemiluminescent imaging system. The results showed there was a very good linear correlation between response and amount of alpha-IFN in the range 1.3-156.0 pg mL(-1) (R = 0.9991) and the detection limit was 0.8 pg mL(-1) (S/N=3). The relative standard deviation (n = 9) was 4.7%. The proposed method has been used for successful analysis of the amount of alpha-IFN in human serum. The results obtained compared well with those obtained by conventional colorimetric ELISA and luminol chemiluminescent ELISA.

Improved Synthesis of Benzotriazoles and 1-Acylbenzotriazoles by Ultrasound Irradiation

Some 1H-benzotriazoles have been synthesised in good yields in short times by reaction of ophenylenediamine with sodium nitrite in acetic acid under ultrasound irradiation. Also, the ultrasoundassisted preparation of 1-acylbenzotriazoles is described. Keywords: Benzotriazoles, acylbenzotriazoles, ultrasound irradiation, sonochemistry, heterocycles

An expeditious synthesis of benzimidazole derivatives catalyzed by Lewis acids

An expeditious and efficient route for the synthesis of benzimidazole derivatives by the reaction of o-phenylenediamines with orthoesters in the presence of Lewis acids was described. ZrCl4, SnCl4 · 5H2O, TiCl4, BF3 · Et2O, ZrOCl2 · 8H2O and HfCl4 exhibited high catalytic activity for this transformation.

The reaction of o-phenylenediamine with α,β-unsaturated carbonyl compounds

The structures of the products obtained by the reaction of o-phenylenediamine and two isomeric chalcones have been identified as 1,5-benzodiazepines. A 1 H, 13 C and 15 N NMR study in solution combined with B3LYP/6-31G** calculations allowed to determine the conformations present in solution.

Ultrasound enhanced synthesis of 1,5-benzodiazepinic heterocyclic rings

1,5-Benzodiazepines are synthesized by a reaction of o-phenylenediamines with a diketone or ketones series by ultrasound irradiation in presence of APTS. The condensation occurred in a mild condition with good to excellent yields.

Synthesis and tuberculostatic activity of new benzimidazole derivatives

The reactions of o-phenylenediamine and 3,4-diaminotoluene with such acids as 3-cyclohexylpropionic, 4-phenylbutyric, 4-cyclohexylbutyric, 3,3-diphenylpropionic, and 3,4-dimethoxyphenylacetic resulted in the formation of the corresponding 2-substituted benzimidazoles. These compounds were transformed into methane-and benzenesulfonamide derivatives. The benzimidazole derivatives obtained were tested in vitro for their tuberculostatic activity. Compounds with good activity (MIC 6.2-25 µg/ml) have been found.

Selective synthesis of 2-aryl-1-arylmethyl-1 H-1,3-benzimidazoles in water at ambient temperature

A highly selective synthesis of 2-aryl-1-arylmethyl-1 H-1,3-benzimidazoles from the reaction of o-phenylenediamines and aromatic aldehydes in the presence of silica sulfuric acid is reported. The reactions were performed in ethanol or water and the catalyst could be reused for several runs.

Solid acid catalytic synthesis of 1,5-benzodiazepines: A highly improved protocol

1,5-benzodiazepines were synthesized from the reaction of o-phenylenediamine and ketones in the presence of heterogeneous catalysis of synthetic and natural zeolites under mild conditions in very good yields and high selectivity.

A Facile Synthesis of 2-Acyl and 2-Alkylaminobenzimidazoles for 5-Lipoxygenase Inhibitors

2-Acylaminobenzimidazoles (2a-r) have been synthesized from o-phenylenediamines (4) with benzoylcarbonimidodithioic acid dimethyl ester (5a) or isobutyrylcarbonimidodithioic acid dimethyl ester (5b) in good yield. 2-Alkylaminobenzimidazoles could be prepared by the reaction of o-Phenylenediamines (4a, b) with benzyl isothiocyanate in moderate yields 8a, b or the reaction of 2-chlorobenzimidazole (9) with benzylamines (10a, b) in moderate yield 11a, b. Finally, the carbamate derivative of 2-aminobenzimidazole (13) was prepared by the reaction with pseudourea (12) in low yield. Most of the prepared analogues were evaluated in leukotriene inhibition assay and it found that benzamide derivatives (2a-i) are quite active among others.

Reaction of 1,3‐Dicarbonyl Compounds with o‐Phenylenediamine or 3,3′‐Diaminobenzidine in Water or under Solvent‐Free Conditions via Microwave Irradiation.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Reaction of 1,3‐dicarbonyl compounds with o‐phenylenediamine or 3,3′‐diaminobenzidine in water or under solvent‐free conditions via microwave irradiation

AbstractReaction of ophenylenediamine with β‐diketones or β‐ketoesters in water formed 2‐substituted benzimi‐dazoles. Reaction of 3,3′‐diaminobenzidine gave similar results. Under microwave irradiation conditions solvent‐free reaction of o‐phenylenediamine with β‐ketoesters afforded l,5‐benzodiazepin‐2‐one derivatives. An exception is the reaction of o‐phenylenediamine with ethyl acetoacetate under microwave irradiation, which gave 2‐methylbenzimidazole.

Metal Ion Directed Synthesis of 12 and 14-Membered Tetraaza Macrocyclic Complexes and their Physico-Chemical Studies

The template condensation reaction of o-phenylenediamine with 2,3-butanedione or 2,4-pentanedione resulted in the formation of new series of 12 and 14-membered tetraaza macrocyclic complexes: [ML1Cl2], [ML2Cl2] [M=Co(II), Ni(II) and Zn(II)]; [CuL1]Cl2 and [CuL2]Cl2. The formation of the macrocyclic framework and the overall geometry of the complexes have been characterized by elemental analyses, FT-IR, 1HNMR, UV-Visible, magnetic susceptibility and conductivity measurements. The copper(II) complexes exhibit square planar geometry, whereas an octahedral geometry is suggested for all other complexes.

Identification of intermediate and product from methemoglobin-catalyzed oxidation of o-phenylenediamine in two-phase aqueous?organic system

Methemoglobin (metHb) was used as a mimetic enzyme for peroxidase to catalyze the oxidation reaction of o-phenylenediamine (OPDA) with H2O2 functioning as an oxidant. A reaction intermediate was obtained in two-phase aqueous-organic system and an absorption peak at 710 nm was confirmed to be that of the intermediate in relation to OPDA. The isolated product and intermediate were characterized by UV-Vis and IR spectrophotometry and HPLC-tandem mass spectrometry. The results showed that the product is 2,3-diaminophenazine, the molecular mass of the intermediate is 212 daltons, and a conceivable structure of the intermediate is suggested. Combining the catalyzed reaction mechanism of peroxidase and our experimental results, a conceivable oxidation reaction mechanism of OPDA and H2O2 using metHb as catalyst is proposed.

A novel one-pot two-component synthesis of tricyclic pyrano[2,3- b]quinoxalines

A one-pot two-component synthesis of tricyclic pyrano[2,3- b]quinoxalines with a pendant hydroxymethyl fuction at the 2-position relevant to molybtopterin is described by the reaction of o-phenylenediamine and phenylhydrazone derivatives of sugars in good yields.