ChemInform Abstract: AMIDINES IN TETRAZOLE SYNTHESIS

Гапоник, П. Н.; Grigor’ev, Yu. V.; Karavai, V. P.

doi:10.1002/chin.198536191

Cited by 6 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2-Bis(1-tetrazolyl)ethane, [14] 1-methyl-1,2-bis(1-tetrazolyl)ethane, [15] and 1,2-bis(1-tetrazolyl)butane [16] were prepared by using literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Alkyl‐Bridged Bis‐5‐azidotetrazoles: A Safe Way of Preparation

Klapötke¹,

Sproll²

2009

Eur J Org Chem

View full text Add to dashboard Cite

The general, high-yielding synthesis of extremely dangerous alkylated bis-5-azidotetrazoles is presented. The preparation using 5-bromotetrazoles for the generation of tetrazolyl hydrazines, which are then converted into the corresponding bis-5-azidotetrazoles, presents a safe, large-scale preparation of alkylated bis-5-azidotetrazoles. In this work, 1,2-bis(5-azido-1H-tetrazol-1-yl)ethane, 1,2-bis(5-azido-1H-tetrazol-1-yl)-1-methylethane, and 1,4-bis(5-azido-1H-tetrazol-1-yl)butane were synthesized and characterized by 1 H, 13 C, and 15 N

show abstract

“…1,2-Bis(1-tetrazolyl)ethane, [14] 1-methyl-1,2-bis(1-tetrazolyl)ethane, [15] and 1,2-bis(1-tetrazolyl)butane [16] were prepared by using literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Alkyl‐Bridged Bis‐5‐azidotetrazoles: A Safe Way of Preparation

Klapötke¹,

Sproll²

2009

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The attempts to perform mercuration of 2-monosubstituted tetrazoles under similar conditions were unsuccessful [11,14] apparently because of lower CHacidity of these tetrazoles compared to the 1-monosubstituted derivatives [14][15][16][17]. A mecuration of 1,3-diaryltetrazolium salts was described to occur at their heating with mercury(II) acetate in DMSO affording bis(tetrazolio)mercury(II) salts [18].…”

Section: -Metallated Tetrazolesmentioning

confidence: 99%

“…The structure of salts 3 was confirmed by the data of 13 C [18] and 119 Hg [19] NMR. Compounds 1 (R = Me, Ph) were obtained in fairly good yields (85-95%) by treating appropriate tetrazoles with a system mercury(II) bromide-lithium bromidesodium hydroxide in aqueous DMF or DMSO [11,13]. Under the above conditions the mercuration occurred yielding only symmetric mercury derivatives.…”

Section: -Metallated Tetrazolesmentioning

confidence: 99%

“…Under the above conditions the mercuration occurred yielding only symmetric mercury derivatives. In a neutral (water) and acid (acetic acid) environment the mercuration of 1-monosubstituted tetrazoles proceeded under more stringent conditions (at boiling), and depending on the reagents ratio bis-or monotetrazolyl mercury derivatives 1 and 2 were obtained [11]. X = Br, OAc; 1, R = Me (80%), t-Bu (80%), All (75%), Ph (85%), Vin.…”

Section: -Metallated Tetrazolesmentioning

confidence: 99%

“…Bis (5-tetrazolyl)mercury derivatives 1 were pepared from 1-monosubstituted tetrazoles and mercury(II) salts in the presence of potassium hydroxide in the lower alcohols (methanol, 2-propanol) at room temperature [11,12].…”

Section: -Metallated Tetrazolesmentioning

confidence: 99%

See 2 more Smart Citations

Organometallic Tetrazole Derivatives: Preparation and Application to Organic Synthesis

2005

Self Cite

View full text Add to dashboard Cite

show abstract

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Войтехович

Vorob'ev

Гапоник

et al. 2005

Chem Heterocycl Compd

Self Cite

View full text Add to dashboard Cite

Keywords: 1-R-5-aminotetrazoles, N-arylcyanamides, 1-R-tetrazoles.C-and N-tetrazolyl groups enter into the composition of a series of biologically active compounds, many of which are used in medicinal practice [1,2]. This is linked primarily with the unique structure of the tetrazole ring which, depending on the location of substituents, may be a bioisostere of a carboxyl or an amide grouping, possessing several advantages over them [2,3]. One of the most preferred routes for making a 1-monosubstituted tetrazole ring is the heterocyclization of primary amines with triethyl orthoformate and sodium azide [3]. This process is used for the synthesis of tetrazoles, starting from primary amines of various nature, including aliphatic, aromatic, and heterocyclic [4][5][6][7][8][9]. It was shown that the reaction proceeds smoothly with the participation of only the simplest alkyl and aryl amines. It was discovered that 2,4-dinitroaniline does not react [7], and in the case of ortho-phenylenediamine the process stops at the stage of forming benzimidazole, the condensation product of triethyl orthoformate with the initial amine [6]. Under analogous conditions thiosemicarbazide forms a 2-aminothiadiazole [7]. Conversion products of several other compounds with a primary amino group, including hydrazine, phenylhydrazine, melamine, and aminoguanidine, failed to be identified [7]. The behavior of other functionally substituted primary amines has not been studied up to the present time, in spite of the obvious effect of the nature of the substituent on the course of the heterocyclization reaction.In the development of these investigations and with the aim of broadening the preparative possibilities of this reaction, the heterocyclization of some alkyl-, aryl-, and hetarylamines has been studied in this work. These include substances of a series of widely known pharmaceutical preparations possessing antibacterial and antiviral action, comprising sulfanilamide, sulfaethidole, sulfadimidine, rimantadine, etc. It was discovered that primary amines 1 react with sodium azide and triethyl orthoformate in acetic acid at a molar ratio of reactants of 1:1.1:3, forming the corresponding 1-monosubstituted tetrazoles 2.

show abstract

ChemInform Abstract: AMIDINES IN TETRAZOLE SYNTHESIS

Abstract: Die N,N′‐substituierten Amidine (I) reagieren mit Natriumazid in Essigsäure zu den Tetrazolen (II).

Cited by 6 publications

References 0 publications

Alkyl‐Bridged Bis‐5‐azidotetrazoles: A Safe Way of Preparation

Alkyl‐Bridged Bis‐5‐azidotetrazoles: A Safe Way of Preparation

Organometallic Tetrazole Derivatives: Preparation and Application to Organic Synthesis

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

Contact Info

Product

Resources

About