71232-25-2

Upstream product

• 506-68-3 bromocyane 
• 95-68-1 2,4-Xylidine 
• 56615-73-7 C₆H₁₅N*C₉H₁₁NS₂ 
• 39842-01-8 2,4-dimethylphenylisothiocyanate 
• 4214-28-2 1-iodo-2,4-dimethylbenzene 
• 420-04-2 CYANAMID 
• 83697-77-2 N-(2,4-dimethylphenyl)-N′-benzoylthiourea 
• 16738-20-8 (2,4-dimethylphenyl)thiourea 

Downstream Products

• 500586-75-4 1-(2,4-dimethylphenyl)-5-amino-1H-tetrazole 
• 857751-07-6 N-(2,4-dimethylphenyl)-1H-tetrazol-5-amine 
• 857751-07-6 5-(2,4-dimethylphenyl)amino-1H-tetrazole 

Relevant academic research and scientific papers

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives

We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.

Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations

An expansion of methodologies aimed at the formation of versatile organonitriles, via the intramolecular aminocyanation of unactivated alkenes, is herein reported. Importantly, the need for a rigid tether in these reactions has been obviated. The ease-of-synthesis and viability of substrates bearing flexible backbones has permitted for diastereoselective variants as well. We demonstrated the utility of this methodology with the formation of pyrrolidones, piperidinones, isoindolinones, and sultams. Furthermore, subsequent transformation of these motifs into medicinally relevant molecules is also demonstrated. A double crossover 13C-labeling experiment is consistent with a fully intramolecular cyclization mechanism. Deuterium labeling experiments support a mechanism involving syn-addition across the alkene.

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.

The synthesis of aryl cyanamides through C-N cross-coupling

The methodology for the preparation of aromatic cyanamides has been demonstrated. The present method involves consecutive desulphurization/C-N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been explored.

The synthesis of arylcyanamides: A copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy

A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thiourea via desulphurization/C-N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described. Various iodobenzenes could give their respective C-N cross-coupled products in good to excellent yields under optimized reaction conditions. Further, the substrate scope has been explored.

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2

An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.

Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides

We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).

An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent

In a one-pot strategy we have achieved an efficient method for the synthesis of organic cyanamides starting from dithiocarbamic acid salts/amines. In this strategy the in situ generated alkyl or aryl isothiocyanates, obtained by the desulfurization of dithiocarbamic acid salts with diacetoxyiodobenzene (DIB) react with aqueous ammonia forming alkyl or aryl thiourea which on subsequent oxidative desulfurization with DIB led to the formation of corresponding cyanamide in good yields. Mild reaction conditions, shorter reaction time, an environmentally benign protocol, and easy isolation of the desired product make the present methodology a suitable alternative for the preparation of various organic cyanamides.