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Journal articles on the topic 'Tetrazole-azide equilibrium'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Līpiņš, Dāgs Dāvis, Andris Jeminejs, Una Ušacka, Anatoly Mishnev, Māris Turks, and Irina Novosjolova. "Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium." Beilstein Journal of Organic Chemistry 20 (March 28, 2024): 675–83. http://dx.doi.org/10.3762/bjoc.20.61.

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2-Chloro-4-sulfonylquinazolines undergo functional group swap when treated with an azide nucleophile: 1) the azide replaces the sulfonyl group at the C4 position; 2) the intrinsic azide–tetrazole tautomeric equilibrium directs the nucleofugal sulfinate from the first step to replace chloride at the C2 position. This transformation is effective with quinazolines bearing electron-rich substituents. Therefore, the title transformations are demonstrated on the 6,7-dimethoxyquinazoline core, which is present in pharmaceutically active substances. The methodology application is showcased by transfor

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2

Abu-Eittah, Rafie H., Sabry El-Taher, Walid M. I. Hassan, and Mahmoud A. Noamaan. "A structural study on the azide–tetrazole equilibrium in the azidobenzothiazole system. DFT-treatment." Computational and Theoretical Chemistry 1033 (April 2014): 52–59. http://dx.doi.org/10.1016/j.comptc.2014.01.024.

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3

Lakshman, Mahesh K., Manish K. Singh, Damon Parrish, Raghavan Balachandran, and Billy W. Day. "Azide−Tetrazole Equilibrium of C-6 Azidopurine Nucleosides and Their Ligation Reactions with Alkynes." Journal of Organic Chemistry 75, no. 8 (2010): 2461–73. http://dx.doi.org/10.1021/jo902342z.

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4

Thomann, A., J. Zapp, M. Hutter, M. Empting, and R. W. Hartmann. "Steering the azido–tetrazole equilibrium of 4-azidopyrimidines via substituent variation – implications for drug design and azide–alkyne cycloadditions." Organic & Biomolecular Chemistry 13, no. 43 (2015): 10620–30. http://dx.doi.org/10.1039/c5ob01006c.

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Variations of substituents at 2-substituted 4-azidopyrimidines allowed us to shift the azido–tetrazole equilibrium to either of the two constitutional isomers. This can be exploited for click chemistry and fragment-based drug design.

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5

Leškovskis, Kristaps, Anatoly Mishnev, Irina Novosjolova, and Māris Turks. "SNAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines." Molecules 27, no. 22 (2022): 7675. http://dx.doi.org/10.3390/molecules27227675.

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A straightforward method for the synthesis of 5-substituted tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines from 2,4-diazidopyrido[3,2-d]pyrimidine in SNAr reactions with N-, O-, and S- nucleophiles has been developed. The various N- and S-substituted products were obtained with yields from 47% to 98%, but the substitution with O-nucleophiles gave lower yields (20–32%). Furthermore, the fused tetrazolo[1,5-a]pyrimidine derivatives can be regarded as 2-azidopyrimidines and functionalized in copper(I)-catalyzed azide-alkyne dipolar cycloaddition (CuAAC) and Staudinger reactions due to the presence of a

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6

Abu-Eittah, Rafie H., and Khaled E. El-Kelany. "A theoretical DFT study on the structural parameters and azide–tetrazole equilibrium in substituted azidothiazole systems." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 99 (December 2012): 316–28. http://dx.doi.org/10.1016/j.saa.2012.08.012.

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7

Sirakanyan, Samvel N., Domenico Spinelli, Athina Geronikaki, Anush A. Hovakimyan, and Azat S. Noravyan. "New heterocyclic systems derived from pyridine: new substrates for the investigation of the azide/tetrazole equilibrium." Tetrahedron 70, no. 45 (2014): 8648–56. http://dx.doi.org/10.1016/j.tet.2014.09.047.

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8

Wael, A. Zordok. "The effect of 6-substituent on isomerization of tetrazolo[1,5-α]pyridines and conformational analysis of 2-azidopyridines : A DFT study". Journal of Indian Chemical Society Vol. 90, Feb 2013 (2013): 197–209. https://doi.org/10.5281/zenodo.5767626.

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Chemistry Department, University College of Quanfudha, Umm Al-Qura University, Kingdom of Saudi Arabia Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt <em>E-mail</em> : waelzordok@yahoo.com Fax : 20-106256488 <em>Manuscript received online 28 March 2012, revised 15 April 2012, accepted 24 April 2012</em> The phenomenon of ring-chain isomerism and conformation are important aspects of chemistry. The effect of substituents CH<sub>3</sub>, OH, CI, OH, CN and NO<sub>2</sub> at the 6-position of tetrazolo[1,5-α]pyridines, on the ring opening of tetrazole to<em> ci

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9

Scapin, Elisandra, Paulo R. S. Salbego, Caroline R. Bender, et al. "Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines." Beilstein Journal of Organic Chemistry 13 (November 10, 2017): 2396–407. http://dx.doi.org/10.3762/bjoc.13.237.

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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

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10

Sirakanyan, Samvel N., Domenico Spinelli, Athina Geronikaki, Anush A. Hovakimyan, and Azat S. Noravyan. "ChemInform Abstract: New Heterocyclic Systems Derived from Pyridine: New Substrates for the Investigation of the Azide/Tetrazole Equilibrium." ChemInform 46, no. 14 (2015): no. http://dx.doi.org/10.1002/chin.201514215.

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11

Sirakanyan, Samvel N., Domenico Spinelli, Athina Geronikaki, et al. "The azide/tetrazole equilibrium: an investigation in the series of furo- and thieno[2,3-e]tetrazolo[3,2-d]pyrimidine derivatives." Tetrahedron 72, no. 16 (2016): 1919–27. http://dx.doi.org/10.1016/j.tet.2016.02.048.

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12

Deev, Sergey L., Tatyana S. Shestakova, Zakhar O. Shenkarev, et al. "¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines." Journal of Organic Chemistry 87, no. 1 (2021): 211–22. http://dx.doi.org/10.1021/acs.joc.1c02225.

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13

Shestakova, Tatyana S., Zakhar O. Shenkarev, Sergey L. Deev, et al. "Long-Range 1H–15N J Couplings Providing a Method for Direct Studies of the Structure and Azide–Tetrazole Equilibrium in a Series of Azido-1,2,4-triazines and Azidopyrimidines." Journal of Organic Chemistry 78, no. 14 (2013): 6975–82. http://dx.doi.org/10.1021/jo4008207.

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14

Deev, Sergey L., Zakhar O. Shenkarev, Tatyana S. Shestakova, Oleg N. Chupakhin, Vladimir L. Rusinov, and Alexander S. Arseniev. "Selective15N-Labeling and Analysis of13C−15NJCouplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines." Journal of Organic Chemistry 75, no. 24 (2010): 8487–97. http://dx.doi.org/10.1021/jo1017876.

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15

Krivopalov, V. P., V. I. Mamatyuk, and E. B. Nikolaenkova. "Effect of intramolecular hydrogen bond on the azide-tetrazole equilibrium of 5-(2?-hydroxyphenyl)tetrazolo[1,5-a]pyrimidine,-tetrazolo[1,5-c]pyrimidme, -tetrazolo[1,5-c]quinazoline, and 7-(2?-hydroxyphenyl)tetrazolo[1,5-c]pyrimidine." Russian Chemical Bulletin 44, no. 8 (1995): 1435–43. http://dx.doi.org/10.1007/bf00714425.

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16

Leškovskis, Kristaps, Anatoly Mishnev, Irina Novosjolova, and Māris Turks. "Structural Study of Azide-Tetrazole Equilibrium in Pyrido[2,3-d]pyrimidines." Journal of Molecular Structure, July 2022, 133784. http://dx.doi.org/10.1016/j.molstruc.2022.133784.

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17

Bucevičius, Jonas, and Sigitas Tumkevičius. "2,4-Diazidopyrrolo[2,3-d]pyrimidines: synthesis, ring–chain tautomerism and Cu(I)-catalyzed azide–alkyne cycloaddition reaction." Chemija 26, no. 2 (2015). https://doi.org/10.6001/chemija.2015.26.2.9.

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2,4-Diazidopyrrolo[2,3-d]pyrimidines were synthesized by the reaction of the corresponding 2,4-dichloropyrrolo[2,3-d]pyrimidines with sodium azide at room temperature. 2,4-Diazidopyrrolo[2,3-d]pyrimidines were shown to exist in an equilibrium with the corresponding 5-azidopyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine. The proportion of the tetrazole tautomer increases with increasing solvent polarity. The CuAAC reaction of the obtained azides with 3-methylphenyl- and 4-biphenylylethynes afforded the corresponding 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines.

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18

Novosjolova, Irina, Māris Turks, Andris Jeminejs, Svetlana M. Goliškina, Dmitrijs Stepanovs, and Ērika Bizdēna. "Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines." Synthesis, November 12, 2020. http://dx.doi.org/10.1055/s-0040-1706568.

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AbstractNucleophilic aromatic substitution reaction between 4-arylthio-2-chloroquinazolines and NaN3 takes place with an unusual sulfanyl group dance and leads to the formation of 5-(arylthio)tetrazolo[1,5-c]-quinazolines, which do not form the azide tautomer and do not undergo CuAAC reactions with alkynes. On the other hand, 5-azidotetrazolo[1,5-a]quinazoline (formally described as 2,4-diazidoquinazoline) undergoes regioselective nucleophilic aromatic substitution with thiols at C5 and forms 5-(alkyl/arylthio)tetrazolo[1,5-a]quinazolines, the structure of which has been proved by X-ray cryst

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19

"Theoretical Study of the Substituent and Solvent Effects on Azide-Tetrazole Equilibrium of 2-Azido-1,3-benzothiazoles." International Journal of Advances in Chemical Engineering and Biological Sciences 1, no. 1 (2014). http://dx.doi.org/10.15242/ijacebs.c1213031.

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20

HAJOS, GY, A. MESSMER, A. NESZMELYI, and L. PARKANYI. "ChemInform Abstract: SYNTHESIS AND STRUCTURAL STUDY OF AZIDONAPHTHO-AS-TRIAZINES. “ANNELATION EFFECT” IN AZIDE-TETRAZOLE EQUILIBRIA." Chemischer Informationsdienst 16, no. 6 (1985). http://dx.doi.org/10.1002/chin.198506256.

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