A convenient approach for the electrochemical bromination and iodination of pyrazoles

Electrochemical bromination and iodination of some pyrazoles were investigated under constant-current (CC) electrolysis in an undivided electrochemical cell. Anodic oxidation of KX salt produces X2 in-situ which can be consumed as an expedient electrophile in pyrazoles aromatic electrophilic substitution reactions or may participate in an X–N coupling reaction with electrochemically catalyzed pyrazolesox to form the halogenated pyrazoles. All reactions proceeded without the need to use any hazardous reagents or catalysts. The reaction conditions are mild and environmentally compatible.

125I –Amoxicillin preparation as a guide tracer for inflammation detection

The objective of this study is to label Amoxicillin with radioactive iodine (125I-AC) via direct electrophilic substitution to act as a promising tracer for inflammation imaging. The highest labeling yield of 80% was achieved after studying all the parameters affecting the labeling reaction using Iodogen (IG) as an oxidizing agent. Molecular Modeling Structure was done using MOE program to predict the suitable 125I position. The product structure was established by a cold iodination reaction using Iodine-127. Biological evaluation of (125I-AC) was carried out using groups of inflamed mice with different exogenous agents such as E.Coli and Turpentine oil. The (125I-AC) shows an in vitro stability of about 97% after 24 h.While doing in vivo studies over 4 h, the tracer stability of 99% was observed.

The Highly Regioselective Synthesis of Novel Imidazolidin-2-Ones via the Intramolecular Cyclization/Electrophilic Substitution of Urea Derivatives and the Evaluation of Their Anticancer Activity

A series of novel 4-(het)arylimidazoldin-2-ones were obtained by the acid-catalyzed reaction of (2,2-diethoxyethyl)ureas with aromatic and heterocyclic C-nucleophiles. The proposed approach to substituted imidazolidinones benefits from excellent regioselectivity, readily available starting materials and a simple procedure. The regioselectivity of the reaction was rationalized by quantum chemistry calculations and control experiments. The anti-cancer activity of the obtained compounds was tested in vitro.

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

A novel, versatile approach for the synthesis of unsymmetrical 3,3'-diindolylmethanes (DIMs) with a quaternary carbon center has been developed via iodine-catalyzed coupling of trifluoromethyl(indolyl)phenylmethanols with indoles. In contrast to previously reported methods, the new procedure is characterized by chemoselectivity, mild conditions, high yields, and scalability to obtain gram amounts for biological studies. Selected compounds were found to display affinity for cannabinoid receptors, which are promising drug targets for the treatment of inflammatory and neurodegenerative diseases.

Synthesis of Methyl Ester Nitrate from Mahogany Seed Oil (Swietenia mahagoni Linn)

Nitration of methyl ester from mahogany oil (Swietenia mahagoniLinn) can be produced by Methyl Ester Nitrate (MEN), an additive that is useful for increasing Cetane Numbers in diesel fuel. This study aims to determine the yield of MEN that can be produced from mahogany seed oil after esterification, trans-esterification, and nitration and to identify the MEN compounds produced. Mahogany oil is obtained by pressing mahogany seeds and then degumming to remove the gum. Mahogany oil-free gum is esterified using methanol with the mole ratio of oil: methanol (1: 6), then trans-esterified, also using methanol with mole ratio (1:15) and a methyl ester is obtained. Then the methyl ester was nitrated with HNO3, sulfuric acid, and acetic anhydride to obtain a translucent reddish colored MEN product with a yield of 24.99%. The success of the synthesis was shown by the FTIR spectrophotometer in the presence of absorption at 1550 cm-1 which indicated the presence of the C-ONO2 group, the absorption at 1365 cm-1 indicated the presence of the NO2 group, and at 1118 cm-1 indicated the presence of the C-N group. The reaction mechanism that occurs during the predicted nitration reaction is an electrophilic substitution reaction and nucleophilic addition.

INVESTIGATION OF REACTIONS OF INTERACTION OF CELLULOSE NITRIC ESTERS WITH CARBOXYLIC ACID CHLORIDES

The chemical interaction of high-nitrogen cellulose ether with acetic, propionic, butyric and isobutyric acids has been studied. The general laws and features of the electrophilic substitution of functional groups of cellulose nitroesters are revealed. The preferred directions of the chemical interaction of cellulose nitrate with carboxylic acid chlorides are established: O-acylation of nitrate and hydroxyl groups; O-acylation of the glucopyranose ring; O-acylation of the ether bond with depolymerization of the chain of an SC molecule; hydrolysis of nitrate groups; destruction of the chain of a macromolecule of nitric acid ester with the formation of water-soluble organic compounds. The structure, properties and possibilities of using synthesized mixed cellulose ethers were studied. Effective methods have been developed for the chemical modification of cellulose nitrates with carboxylic acid chlorides. The probable directions of the reaction of the interaction of cellulose nitrates with electrophilic reagents are predicted based on quantum-chemical calculations of point charges on the atoms of the reacting molecules. The reactivity of highly substituted cellulose nitrates in reactions with carboxylic acid chlorides has been established. The optimal conditions for the interaction of cellulose nitrates with carboxylic acid chlorides have been identified and a mathematical model of the reaction kinetics has been constructed. The possibility of a directed change in the composition of chemically modified cellulose nitrates depending on the synthesis conditions has been established. As a result of the combined use of physicochemical research methods, the chemical composition was determined and the structure of the synthesized compounds was determined: cellulose acetyl nitrates, cellulose propionyl nitrates, cellulose butyryl nitrates, and cellulose isobutyryl nitrates. Using gel chromatography, it was found that the molecular weight characteristics of the synthesized samples are directly dependent on the conditions of their synthesis. It was found that electrophilic substitution of the functional groups of cellulose nitrate proceeds more intensively in the pyridine medium.

Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

Several new heterocyclic systems based on a hydroxybenzofuro[2,3-b]pyridine building block were prepared. This benzofuropyridine is easily available from the Meerwein reaction of benzoquinone and a heterocyclic diazonium salt, followed by reduction and cyclization. Electrophilic substitution and further condensations give polycyclic systems, including oxazolo- and chromeno-fused analogues.