73565-26-1

Upstream product

• 4418-61-5 5-aminotetrazole 
• 696-62-8 para-iodoanisole 
• 16519-47-4 1,3-di(p-methoxyphenyl)selenourea 
• 1227-45-8 1,3-bis-(p-methoxyphenyl)thiourea 
• 104-94-9 4-methoxy-aniline 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 

Downstream Products

• 1442440-63-2 N-(2-bromo-4-methoxyphenyl)-1-(4-methoxyphenyl)-1H-tetrazol-5-amine 
• 1442440-83-6 N-(2,6-dibromo-4-methoxyphenyl)-1-(4-methoxyphenyl)-1H-tetrazol-5-amine 

Relevant academic research and scientific papers

Temperature dependent regioselective synthesis of aryl tetrazole amines using copper source

One pot highly efficient and simple protocol for the construction of aryl tetrazole amines via desulphurization/substitution/electro cyclization/C-N cross coupling reactions from thiourea with the use of cheap, readily available and air stable copper sour

Cobalt-promoted regioselective preparation of aryl tetrazole amines

Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and 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 demonstrated. Graphical Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and C- N cross-coupling reaction.

Palladium catalyzed carbonylative annulation of the C(sp2)-H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones

Pd(ii) catalyzed direct C-H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields. This methodology offers a convenient method for the synthesis of these important heterocyclic scaffolds in a highly atom economical process. On the mechanistic aspect weakly nucleophilic triazole and tetrazole moieties function as both directing as well as intramolecular nucleophiles. The catalytically active C-H activated intermediate dimeric Pd complex was isolated and characterized which on exposure to CO gas gave the corresponding tetrazole fused quinazolinone derivative. On the basis of isolation of the intermediate and observed kinetic isotope effects, a mechanism has been proposed for the C-H activated direct carbonylative annulation reaction.

Method for preparing 5-aminotetrazole compound

The invention discloses a method for preparing a 5-aminotetrazole compound. The method comprises the following steps: adding bis-substituted selenourea shown in the formula II in the description, ionic liquid loaded iodobenzene diacetate shown in the formula III in the description, sodium azide and alkali A into a solvent B, stirring at -10 to -80 DEG C and conducting cyclization reaction, and after the reaction is finished, conducting aftertreatment on the reaction liquid to prepare the 5-aminotetrazole compound shown in the formula I in the description. Compared with the conventional method, a green reagent, namely, ionic liquid loaded iodobenzene diacetate, is adopted, so that the use of heavy metal is avoided, the operation is simple and convenient, and the reaction yield is high.

Desulfurization strategy in the construction of azoles possessing additional nitrogen, oxygen or sulfur using a copper(I) catalyst

A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper( I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable nucleophiles. For aminotetrazoles and triazoles an excellent regioselectivity has been achieved through proper tuning of the pKa values of the parent amines attached to unsymmetrical thioureas. The method represents an autocatalytic process in which copper( I) iodide gets converted to copper(II) sulfide which in turn transforms to active copper(II) oxide that effectively carries forward the catalytic cycle. The fate of the copper catalyst has also been studied using scanning electron microscopic (SEM) and energy-dispersive X-ray spectroscopic (EDS) analyses which give an insight into the mechanism for this catalytic process.