The azide/tetrazole equilibrium: an investigation in the series of furo- and thieno[2,3-e]tetrazolo[3,2-d]pyrimidine derivatives

Sirakanyan, S. N.; Spinelli, Domenico; Geronikaki, Athina; Карцев, В. Г.; Panosyan, G. A.; Ayvazyan, A. G.; Tamazyan, R. А.; Frenna, Vincenzo; Hovakimyan, Anush A.

doi:10.1016/j.tet.2016.02.048

Cited by 13 publications

(9 citation statements)

References 38 publications

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“…In fact, its 1 H NMR spectrum in DMSO/ CCl 4 (1:3) showed the expected double set of signals: the 8A/T isomer ratio was 3:1. Moreover all of the chemical shifts of the tetrazolo form, as a rule, appeared at lower field then those due to the azido form (Sirakanyan et al 2016b).…”

Section: Chemistrymentioning

confidence: 83%

“…Based on spectroscopic results we can conclude that as the thieno[2,3-e]tetrazolo [1,5-c] pyrimidines (Sirakanyan et al 2016b 8 in the solid state is presents exclusively in the tetrazolo tautomeric form, while in solution it exists as a mixture of two isomeric forms.…”

Section: Chemistrymentioning

confidence: 97%

“…In a previous paper from us (Sirakanyan et al 2016b) we have described the synthesis of thieno[2,3-e]tetrazolo[1,5-c]pyrimidines, the structure of which was determined by the X-ray crystallography, showing that thieno[2,3-e] tetrazolo[1,5-c]pyrimidines in the crystalline state are present exclusively in the tetrazolo tautomeric form. However in solution thieno[2,3-e]tetrazolo-[1,5-c]pyrimidines exist as mixtures of azide and tetrazol isomers (Sirakanyan et al 2016b).…”

Section: Chemistrymentioning

confidence: 99%

“…Furthermore, considering our previous experience in the field of azide-tetrazole equilibrium in the series of thieno[2,3-e]tetrazolo [1,5-c] pyrimidines (Sirakanyan et al 2016b), herein we report the synthesis of new 8-azidothieno[3,2-d] p y r i m i d i n e / t h i e n o [ 2 , 3 -e ] t e t r a z o l o [ 1 , 5 -c ] pyrimidine 8A/T.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Sirakanyan¹,

Geronikaki

Spinelli

et al. 2018

An. Acad. Bras. Ciênc.

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Annulated thienopyrimidine derivatives attracted big interest of the scientific community due to their broad spectrum of biological activities among which are the inhibition of phosphodiesterase, antiproliferative and antimicrobial activities. As a continuation of our studies on the synthesis and biological activity of fused thieno[3,2-d]pyrimidine derivatives, the goal of this paper is the synthesis and study of the properties of compounds containing different heterocycles such as fused thieno[2,3-b]pyridine and tetrazolo[1,5-c]pyrimidine in the same molecule. Thus, starting from the ethyl 1-amino-5-isopropyl-8,8-dimethyl-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate 1, efficient methods for obtaining new 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidines 6 and thieno[2,3-e]tetrazolo[1,5-c]pyrimidine 8 are described. The spectroscopic results showed that compound 8 in the solid state is exclusively in the tetrazolo tautomeric form, while in solution an azide-tetrazole equilibrium is present 8A/T. The possible antimicrobial activity of newly synthesized compounds against some gram-positive and gram-negative bacilli strains has been evaluated. The biological tests evidenced that some of them showed promising antimicrobial activity. Two compounds showed similar activity to the one of the used reference drug. The study of structure-activity relationships revealed that the activity of a compound depends mostly on the nature of substituent R1R2. According to the predicted docking studies our compounds could be DnaG inhibitors.

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Section: Chemistrymentioning

confidence: 83%

Section: Chemistrymentioning

confidence: 97%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Sirakanyan¹,

Geronikaki

Spinelli

et al. 2018

An. Acad. Bras. Ciênc.

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“…In solution, the tetrazole–azido equilibrium is influenced by the polarity of the solvent. Upon increasing the solvent polarity, an increase in the amount of the tetrazole form in equilibrium is usually observed [ 28 , 36 ]. In general, the tetrazole form 3a – g is predominant in the mixture at a proportion greater than 4:1 relative to the azide form 4a – g .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

Scapin

Salbego

Bender

et al. 2017

Beilstein J. Org. Chem.

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An efficient synthesis methodology for a series of tetrazolo[1,5-a]pyrimidines substituted at the 5- and 7-positions from the cyclocondensation reaction [CCC + NCN] was developed. The NCN corresponds to 5-aminotetrazole and CCC to β-enaminone. Two distinct products were observed in accordance with the β-enaminone substituent. When observed in solution, the compounds can be divided into two groups: (a) precursor compounds with R = CF3 or CCl3, which leads to tetrazolo[1,5-a]pyrimidines in high regioselectivity with R at the 7-position of the heterocyclic ring; and (b) precursor compounds with R = aryl or methyl, which leads to a mixture of compounds, tetrazolo[1,5-a] pyrimidines (R in the 5-position of the ring) and 2-azidopyrimidines (R in the 4-position of the ring), which was attributed to an equilibrium of azide–tetrazole. In the solid state, all compounds were found as 2-azidopyrimidines. The regiochemistry of the reaction and the stability of the products are discussed on the basis of the data obtained by density functional theory (DFT) for energetic and molecular orbital (MO) calculations.

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Recent investigations and applications of azidoazomethine-tetrazole tautomeric equilibrium (microreview)

Sebris

Turks

2019

Chem Heterocycl Comp

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The azide/tetrazole equilibrium: an investigation in the series of furo- and thieno[2,3-e]tetrazolo[3,2-d]pyrimidine derivatives

Cited by 13 publications

References 38 publications

Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

Recent investigations and applications of azidoazomethine-tetrazole tautomeric equilibrium (microreview)

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