Najmeh Nowrouzi

Persian Gulf University | PGU · Department of Chemistry

Cyanodithioformate salt as an odorless and simply operational source of sulfur was reacted with aryl halides in the presence of copper iodide, affording diaryl disulfide, which reacted with styrenes/α‐methylstyrene in second step to form β‐Hydroxy sulfides with high regioselectivity in good to excellent yields.

The potential of industrial cobalt phthalocyanines in the synthesis of thioamides is reported. A mixture of an industrial sulfonated cobalt phthalocyanines known as Co[(SO3Na)2,3Pc] (Europhtal catalyst additive 8020) is introduced as an efficient catalyst capable of converting benzyl thiols to synthetically valuable thioamides by reaction with amin...

A simple, efficient, and smooth thiocyanation of indoles, phenols and aniline derivatives using NH4SCN, DMSO and H2SO4 in DMF is introduced. Using this procedure, diverse indoles and N-alkyl indoles are selectively thiocyanated at the C-3 position. para-free anilines, N-alkyl anilines and phenols undergo thiocyanation at the para position selective...

First direct access to thioarylated aminouracils and enaminones from aryl halides in the presence of CuI and potassium cyanodithioformate as an effective source of sulfur, via a process which is...

In this study, an efficient method for the synthesis of new cyclophanes (5a-f, 6a-g) through the condensation of 1,4-phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-diamine (4) with 2-substituted vinamidiniums (2a-g) is described. The cyclophane derivatives are obtained in good to excellent yields in the presence of acetic acid in refl...

A ligand‐free, CuI‐catalyzed protocol was developed for the one‐step preparation of Michael adducts of aromatic thiols in high yields by reacting a mixture of an aryl halide and an electron‐deficient alkene with sodium iso‐propyl xanthogenate. Synthesis of thioethers by a one‐pot, tandem reaction of aryl halides, sodium iso‐propyl xanthogenate, and...

A one-pot efficient synthesis of β-aryl-β-sulfanyl ketones is introduced via a tandem aldol condensation-thia-Michael addition process using NaOH in the poly ethylene glycol (PEG-200). Addition of different thiols in situ generated from the reaction of alkyl halides with thiourea to chalcones, formed in situ from the condensation of acetophenone de...

Pd‐catalyzed synthesis of urea derivatives from aryl iodides and different aliphatic and aromatic amines using sodium azide and chromium hexacarbonyl is described. In this process, carbonylation of aryl iodides, Curtius rearrangement of aroyl azides, and nucleophilic addition of amines sequentially occur to afford the products in good to excellent...

In this study, first direct access to aryl alkyl sulfides employing 2‐phenylpropanal as coupling partner is reported. Diaryl disulfides react with this aldehyde in the presence of morpholine and produce the corresponding sulfide products in high yields. In another part, disulfides are in situ generated in the reaction mixture from aryl halides/CuI/...

A simple and efficient procedure for aerobic oxidation of thiols into symmetric disulfides using Na2S4O6 as catalyst in situ generated by reacting Na2S2O3 with I2 in poly ethylene glycol (PEG‐200) has been introduced. Using this catalyst system, convenient protocol for one‐pot achievement of symmetric disulfides via aerobic oxidation of thiols in s...

A simple and efficient procedure for trimerization of aromatic aldehydes mediated by potassium cyanide is described. A variety of aromatic aldehydes reacted efficiently and the corresponding oxidative esterification products were obtained in good to excellent yields in the absence of oxidant, solvent and metal species. Trimerization of aromatic ald...

In this paper, a one-step copper-catalyzed procedure for oxidative coupling of active methylene compounds including cyclic β-diketones, cyclic β-ketoesters and 5-pyrazolone with benzenethiols is described. Benzenethiols are in situ generated in the reaction mixture from aryl halides and thiourea as sulfur transfer reagent. α-Thioaryl compounds are...

The preparation of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones through three-component reaction of ethyl acetoacetate, hydroxylamine and aromatic aldehydes in the presence of catalytic amounts of 4-(N,N-dimethylamino)pyridinium acetate as a protic ionic compound is described. The reactions proceeded to completion at 70 °C under solvent-free condit...

Copper iodide has been used as catalyst for developing a new route to 3-sulfenylindoles from the reaction of aryl halides with indole derivatives in the presence of thiourea and hexachloroethane...

A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.

A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent y...

A convenient synthesis of substituted spiroindenoquinoxalines at mild and green conditions was developed. Multicomponent reaction of substituted phenylene diamines, ninhydrin, malononitrile and N,N’-substituted-2-nitroethene-1,1-diamines produced the target compounds. Twelve new spiroindenoquinoxalines were obtained, and their ability in inhibition...

A method for the synthesis of diaryl sulfides from aryl halides in polyethylene glycol was reported. Inodorous Na2S2O3·5H2O, which is readily available as a stable salt, is an effective source of sulfur in the presence of CuI as catalyst.

Pyrido[1,2-a]pyrimidinium salt derivatives 2a–f were prepared in good yields by condensation of 2-aminopyridine with 2-substituted vinamidinium salt derivatives 1a–f. The purity and the structure of the synthetized compounds were ascertained by elemental analysis, mass spectrometry, infrared, and NMR (¹H and ¹³C 400 MHz) spectroscopy.

An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the...

A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140 °C in DMF or poly ethylene gl...

Various 5-substituted tetrazoles are obtained under solvent-free reaction conditions.

In this paper the successful application of DABCO both as base and as ligand for efficient coupling reactions of aryl iodides and bromides with 2-hydroxybenzaldehydes in the presence of catalytic amounts of PdCl2 in water as solvent was introduced.

N-(diphenylphosphino)triethyl- and tributylammonium salts are introduced as easily prepared, cheap and stable ionic liquids that act as the condensing agent and media for the efficient esterification of acids with alcohols and phenols. This class of ionic liquids is immiscible with the ester products and thus allows simple and easy separation of th...

A reusable ligand-free palladium catalyzed phosphorylation of aryl iodides using PdCl2/tetrabutylammonium bromide is described. Functionalized triarylphosphines were obtained in good to excellent yields in the absence of external reductants and supporting ligands.

An efficient, inexpensive and reusable NiCl2·6H2O/n-Bu4NBr catalytic system is described for the direct C-H arylation of 2-hydroxybenzaldehydes with aryl iodides for the first time.

Background: Tetrazoles are imperative nitrogen rich heterocyclic compounds with a wide range of applications in the field of organic synthesis, coordination chemistry, material sciences, and medicinal chemistry. A most common approach for the synthesis of 5-substituted-1H-tetrazoles is achieved by [3+2] cycloaddition reaction of azides to nitriles....

An efficient and simple protocol for the Heck reaction of aryl iodides and bromides using NiCl2·6H2O as the pre-catalyst is presented. The reactions proceed well in ethylene glycol in the absence of phosphine ligands and reducing agent. Compared to the frequently used expensive palladium catalysts, the use of nickel catalyst has an economic advanta...

Tetrabutylammonium nitrate is reported as an effective reusable medium, suitable reducing and stabilizing agent for the Heck coupling reaction of aryl iodides and bromides with styrene and n-butyl acrylate. The efficient phosphine-free, palladium-catalyzed homocoupling reaction of aryl iodides and bromides is also demonstrated in the presence of te...

A recyclable bifunctional acid–base organocatalyst with ionic liquid character has been prepared and its catalytic activity for the preparation of oxadiazoles has been investigated.

Palladium-catalyzed CH bond functionalization of 2-hydroxybenzaldehydes.•CC bond formation of 2-hydroxybenzaldehydes with aryl halides.•Excellent efficiency of reaction in water as a green solvent.•An efficient method for the reaction of aryl bromides with 2-hydroxybenzaldehydes.

Amine-based ionic liquids (R3N+PPh2) are reported as an effective reusable medium, suitable Pd(II) ligand and also reducing agent for the Heck coupling reaction of aryl iodides and bromides with styrene and n-butyl acrylate. The ionic liquid, still containing its corresponding Pd(0) complex, was easily recovered and reused in several runs without l...

Acylimidazolium acetate was readily prepared in situ from the reaction of imidazole with acetic anhydride and subsequently acted as a catalyst and acylating agent for the efficient acetylation of alcohols, phenols, and amines at ambient temperature.

The use of N-bromosuccinimide and silver nitrate as a convenient reagent system for the nitration of aromatic compounds under neutral and environmentally safer reaction conditions is described.

The reaction proceeds with aromatic as well as aliphatic carboxylic acids using low-toxic reagents and providing easy work-up.

Chlorodiphenylphosphine, imidazole, and molecular iodine in refluxing dichloromethane are used for the efficient preparation of amides under mild reaction conditions. This reagent system also shows excellent selectivity for mono-N-alkylation of amines with alcohols. In this system, the resulting phosphorus byproduct (diphenylphosphinic acid) is eas...

A mild, efficient and simple method for the preparation of acyl azides from carboxylic acids using chlorodiphenylphosphine in the presence of molecular iodine and sodium azide is described.

The system minimizes the formation of waste products compared to traditional methods and allows the mononitration of various aromatic compounds under mild conditions.

Aromatic compounds were nitrated efficiently under essentially neutral conditions by employing Ph2PCl in the presence of I2 and AgNO3. This method minimizes waste products compared to traditional methods and gives the corresponding mononitro derivatives in good to excellent yields in dichloromethane at room temperature.

Condensation of carboxylic acids with alcohols, phenols and thiols proceeded smoothly to afford carboxylic acid alkyl esters, phenolic esters and thioesters by using the combination of chlorodiphenylphosphine, imidazole and molecular iodine in refluxing acetonitrile. Esterification with this mixed reagent system gave the corresponding products in e...

Selective N-monoalkylation of aromatic amines with 1° and 2° alcohols and conversion of aromatic amines to amides are performed immediately and in excellent yields using triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in dichloromethane at room temperature. Symmetrical and unsymmetrical N,N-dialkylation of aromatic amines a...

The combination PPh3/Br2/n-Bu4NNO2 was developed as a new reagent system for the efficient preparation of N-nitrosamines and azides from the corresponding amines and hydrazine derivatives, respectively, at 0°C to room temperature, in excellent yields.

The use of PPh3/Br2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions.

The use of Ph3P/DDQ offers a novel, neutral and highly efficient method for the efficient conversion of 2-hydroxyaryl aldoximes and ketoximes to 1,2-benzisoxazoles in excellent yields at room temperature.

A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1° and 2° alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3° ones to isothiocyanates in good to high yields.

The use of PPh3/Br2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions.

Alcohols, thiols, and silyl ethers are converted into alkyl azides in good to excellent yields by treatment with PPh 3 /DDQ/ n-Bu 4 NN 3 in CH 2 Cl 2 at room temperature. The method is highly selective for 1° alcohols in the presence of 2° and 3° ones, and also thiols and silyl ethers.

Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu(4)NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room temperature. This method is highly selective for the conversion of 1 degrees alcohols in the presence of 2...

Alcohols, thiols, and silyl ethers are converted into alkyl azides in good to excellent yields by treatment with PPh3/DDQ/n-Bu4NN3 in CH2Cl2 at room temperature. The method is highly selective for 1° alcohols in the presence of 2° and 3° ones, and also thiols and silyl ethers.