One-pot, three-component, iron-catalyzed synthesis of benzimidazoles via domino C-N bond formation.

An efficient one-pot, three-component process for the synthesis of benzimidazole derivatives using a catalytic amount of Fe(iii) porphyrin has been developed. The reaction proceeds via domino C-N bond formation and cyclization reactions of benzo-1,2-quinone, aldehydes and ammonium acetate as a nitrogen source to selectively produce benzimidazole. A number of benzimidazole derivatives have been synthesized using this method in high yields under mild reaction conditions.

Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones via C-C and C-O bond cleavage.

An efficient metal-free synthesis strategy of benzoxazoles was developed via coupling catechols, ammonium acetate, and alkenes/alkynes/ketones. The developed methodology represents an operationally simple, one-pot and large-scale procedure for the preparation of benzoxazole derivatives using molecular iodine as the catalyst.

One-Pot Multicomponent Reaction of Catechols, Ammonium Acetate, and Aldehydes for the Synthesis of Benzoxazole Derivatives Using the Fe(III)-Salen Complex.

The Fe(III)-salen complex has been applied successfully as a catalyst for the novel, simple, efficient, and one-pot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes (nontoxic and cheap alternatives of amines) for the first time. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the presence of a catalyst in EtOH under mild conditions, and all products were obtained in excellent yields. To the best of our knowledge, this method is the first example of the multicomponent synthesis of benzoxazole derivatives using these starting materials. The notable features such as the use of air that is considered as a benign oxidant and EtOH as a green solvent, ease of product separation, readily available and inexpensive aldehydes, and mild conditions make our procedure more efficient and practical for organic synthesis. Moreover, the current protocol is successfully applied to synthesize desirable products on a large scale.

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes.

This review article discusses the progress related to the synthesis and catalytic applications of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials for industrial and laboratory products. These catalysts are widely used in acid-catalyzed processes. Most of these acid catalysts are eco-friendly, reusable, and stable. Moreover, the discovery of unique catalysts is vital for developing new, efficient, and reusable catalysts for industrial and laboratory applications. The aim of this review article is to review the recent studies (2014-2018) in the field of the utility of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials for developing acidic catalysts.

Synthesis and biological evaluation of some novel diastereoselective benzothiazole ß-lactam conjugates.

Highly diastereoselective synthesis of some novel benzothiazole-substituted ß-lactam hybrids was achieved starting from (benzo[d]thiazol-2-yl)phenol as an available precursor. This is the first time (benzo[d]thiazol-2-yl)phenoxyacetic acid has been used as ketene source in synthesizing monocyclic 2-azetidinones. These compounds were evaluated for their antimicrobial activities against a large panel of Gram-positive and Gram-negative bacterial strains and moderate activities were encountered. Antimalarial data revealed that adding methoxyphenyl or ethoxyphenyl group on the ß-lactam ring makes compounds that are more potent. Moreover, hemolytic activity and mammalian cell toxicity survey of the compounds showed their potential as a medicine.

Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H.

A highly efficient, simple and environmentally friendly synthesis of 3-arylquinolines has been developed in the presence of Al2O3/MeSO3H via one-pot reaction of anilines and styrene oxide. This methodology provides very rapid access to 3-arylquinolines in good to excellent yields under solvent-free conditions at room temperature in air.

Cu(II) complex of pyridine-based polydentate as a novel, efficient, and highly reusable catalyst in C-N bond-forming reaction.

In this paper, a highly reusable copper(II) complex of pyridine-based polydentate is able to efficiently catalyze a C-N bond-forming reaction under mild conditions. A variety of N-heterocyclic and amine compounds arylated with different aryl iodides, bromides, and chlorides produced N-substituted compounds in good to excellent yields. This methodology can be also used for the arylation of N-unsubstituted compounds using arylboronic acids under solvent-free conditions. All reactions are performed in short times under air, and the catalyst can be reused up to seven times.

A mild, three-component one-pot synthesis of 2,4,5-trisubstituted imidazoles using Mo(IV) salen complex in homogeneous catalytic system and Mo(IV) salen complex nanoparticles onto silica as a highly active, efficient, and reusable heterogeneous nanocatalyst.

Mo(IV) salen complex (2.5 mol%) was found to be a highly efficient catalyst for the one-pot synthesis of 2,4,5-triarylimidazoles via a three-component reaction using benzil or benzoin, aryl aldehydes, and ammonium acetate as a nitrogen source under mild conditions. In order to recover and the reuse of the catalyst, a new Mo(IV) salen-silica nanoparticle as heterogeneous catalyst was prepared by simple and successful immobilization of the catalyst onto silica (3-aminopropyl functionalized silica gel). This procedure can be applied to large-scale conditions with high efficiency. Experimental evidence showed that the catalyst is stable and can be easily recovered and reused for at least five times without significant loss of activity. The nanocatalyst was characterized using FT-IR spectroscopy, scanning electron microscopy, atomic force microscopy, powder X-ray diffraction , transmission electron microscopy, thermogravimetric instrument for analysis of nitrogen adsorption, and inductively coupled plasma spectrometer.

An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions.

In this work, the combination of 7,8-dihydroxy-4-methyl coumarin (DHMC) as a novel bidentate O,O-chelating agent and copper(II) acetate monohydrate (2:1 molar ratio) has been found to form an efficient catalytic system. This catalyst provided good to excellent yields in the multi-component click synthesis of 1,4-disubstituted-1,2,3-triazoles by using various structurally diverse organic halides, different non-activated terminal alkynes, and sodium azide. This catalytic system eliminates the need for the isolation of the hazardous azide intermediates which are generated in situ. The reaction is carried out in aqueous phase at room temperature and it can be accelerated by sonication or by increasing the reaction temperature. Moreover, the reaction can be performed in large scale. It is noteworthy that DHMC is commercially available and that it can be easily synthesized with low cost materials.

2-[(E)-(Morpholin-4-yl-imino)-meth-yl]-6-(morpholin-4-ylmeth-yl)phenol.

The title compound, C16H23N3O3, contains two morpholine rings, each of which adopts a chair conformation. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, leading to a S(6) ring. In the crystal, mol-ecules are linked into zigzag chains along the c-axis direction by C-H⋯O and C-H⋯π inter-actions.

2-[(E)-(4-Methyl-phen-yl)imino-meth-yl]-6-(morpholin-4-ylmeth-yl)phenol.

In the title compound, C(19)H(22)N(2)O(2), the morpholine ring adopts an almost perfect normal chair conformation with puckering parameters Q(T), θ and ϕ of 0.5642 (18) Å, 177.32 (17) and ϕ = 10 (4)°, respectively. The two benzene rings make a dihedral angle of 42.67 (8)° with each other. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular conformation. Aromatic C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distance = 3.6155 (15) Å] between the benzene rings contribute to the stabilization of the crystal structure.