622-34-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1045, 1981 DOI: 10.1021/jo00318a049

InChI:InChI=1/C7H6N2/c8-6-9-7-4-2-1-3-5-7/h1-5,9H

Upstream product

• 5378-52-9 phenyl-1H-tetrazole 
• 103-85-5 monophenylthiourea 
• 64-17-5 ethanol 
• 6919-35-3 N-hydroxy-N'-phenyl-thiourea 
• 64-10-8 phenyl carbamate 
• 2244-91-9 1,4-diphenyl-1,4-dihydro-1,2,4,5-tetrazine 
• 75307-67-4 2,2-dimethyl-[1,3]dioxane-4,5,6-trione-5-phenylhydrazone 
• 56476-95-0 2-phenyl-2H-tetrazole 
• 3663-37-4 3-phenyl-1,2,4-oxadiazol-5-amine 
• 6017-59-0 3-methyl-4-phenylhydrazonoisoxazol-5-one 
• 7758-99-8 copper(II) sulfate 
• 546-67-8 lead(IV) tetraacetate 
• 103-72-0 phenyl isothiocyanate 
• 142-71-2 copper diacetate 

Downstream Products

• 102-03-4 1-acetyl-3-phenylurea 
• 17823-27-7 2-phenylaminothiazol-4-one 
• 57469-23-5 N-cyano-N-phenylbenzenesulfonamide 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 98997-21-8 N-phenylcarbamimidoyl-glycine 
• 39536-15-7 O-methyl-N-phenyl-isourea 
• 64-10-8 phenyl carbamate 
• 4427-60-5 Phenyldicyanamid 
• 39536-17-9 O-ethyl-N-phenyl-isourea 
• 740768-89-2 1,2,5-triphenyl-biguanide 
• 127213-68-7 N-phenyl-N'-p-tolyl-guanidine 
• 6268-14-0 N-phenyl-N'-o-tolyl-guanidine 
• 42544-37-6 N-Methyl-N'-phenyl-guanidin 
• 102-06-7 diphenylguanidine 

Relevant academic research and scientific papers

The Photolysis of 2-Phenyltetrazole

The photolysis of 2-phenyltetrazole (1) in benzene yields phenylcyanamide (27percent) and the phenylhydrazone of o-aminobenzoyl cyanide (53percent) whose structure was determined by X-ray crystal structure analysis.

On Reactions of 5-Imino-N,4-diaryl-4,5-dihydro-1,2,4-thiadiazol-3-amines with Phenylethynyl Sulfones

Abstract: N-Arylthioureas were reacted with hydrogen peroxide to synthesize 5-imino-N,4-diaryl-4,5-dihydro-1,2,4-thiadiazol-3-amines (Ar = Ph, p-Tol, 4-BrC6H4). The products undewent 1,3-dipolar cycloaddition to (R-ethynyl)sulfonyl b

Cyanide-Free Synthesis of Air Stable N-Substituted Li and K Cyanamide Salts from Tetrazoles. Applications toward the Synthesis of Primary and Secondary Cyanamides as Precursors to Amidines

A practical two-step synthesis of N,N′-disubstituted cyanamides consists in the low-temperature metalation of N-substituted 5H-tetrazoles that undergo spontaneous cycloreversion at 0 °C releasing dinitrogen, and forming N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Remarkably, the N-substituted Li and K cyanamides are air stable white solids at room temperature. Addition of lithium organometallics to the N,N′-disubstituted cyanamides provides a new method for accessing N,N′-disubstituted amidines.

Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides

A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.

CF3SO2Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO2 Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines

An unprecedented electrochemical trifluoromethylation/SO2 insertion/cyclization process has been achieved in an undivided cell in an atom-economic fashion. The protocol relies on tandem cyclization of N-cyanamide alkenes by using Langlois’ reagent as a source of both CF3 and SO2 under direct anodically oxidative conditions, in which two C?C bonds, two C?X bonds (N?S and S?C), and two rings were formed in a single operation. This transformation enabled efficient construction of various trifluoromethylated cyclic N-sulfonylimines from readily accessible materials.

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Photolysis and Pyrolysis of Phenyltetrazoles: Formation of Phenylcarbodiimide, N-Phenylnitrile Imine, Phenylnitrene, Indazole, and Fulvenallene

Photolysis of 1-phenyltetrazole 2b at either 193 or 266 nm in a Ne matrix as well as flash vacuum pyrolysis (FVP) of the same compound with isolation of the products in Ne matrix generate phenylcarbodiimide PhN=C=NH 6 very efficiently as the principal product in an almost pure state. Minor amounts of phenyl azide 8 and 1-azacyclohepta-1,2,4,6-tetraene 10, the product of ring expansion of phenylnitrene, are also formed, and the amounts of both substances increase as a function of photolysis time. The photolysis of 2-phenyltetrazole 1b in a Ne matrix at 266 nm for 0.5 min generates the allenic N-phenylnitrile imine PhN=N(+)=CH(–) 3b, absorbing strongly and cleanly at 2021 cm–1 in the IR spectrum. At longer photolysis times peaks ascribed to phenyl azide, phenylnitrene, 1-azacycloheptatetraene, and phenylcarbodiimide 6 become prominent. FVP of 2-phenyltetrazole yields indazole 15 as the major product together with a small amount of phenylcarbodiimide 6. Indazole formation is ascribed to cyclization of the nitrile imine in the ground state. It is not formed on FVP of 1-phenyltetrazole in agreement with the computational result that the thermodynamically most favourable path for rearrangement of the putative N-phenylimidoylnitrene 5b yields phenylcarbodiimide 6 rather than phenylnitrile imine 3b. Further pyrolysis of indazole affords a minor yield of fulvenallene 18.

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

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.