Structural Proof of Tetrazolo[1,5-a]quinazoline Derivatives and their Application in the Synthesis of 4-Amino-2-(1,2,3-triazol-1-yl)quinazolines*

Kalniņa, Agnese; Bizdēna, Ērika; Kiseļovs, Gļebs; Mishnev, Anatoly; Turks, Māris

doi:10.1007/s10593-014-1418-2

Cited by 13 publications

(13 citation statements)

References 17 publications

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“…In entries 11 , 12 , 13 , and 16 , azido‐tetrazole equilibrium occurs at 2, 4, and 6 positions of pyrimidine ring, due to the availability of ortho ‐ N for isomerization . The factors like substituents, polar solvents, high temperature, and steric effect maintain the azido‐tetrazole equilibrium as observed in compounds 11 a , 12 a , 13 a , and 16 a . Therefore, the formation of ‐N 3 favors azido‐tetrazole equilibrium that is independent of synthetic mechanism either by substitution of –NH 2 or from the chloro group.…”

Section: Resultsmentioning

confidence: 86%

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Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

et al. 2020

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A new family of pyrimidine modified tetrazole & azido derivatives (1-16) was developed using the conventional and nucleophilic substitution methods. The 1H-tetrazol-1-yl)pyrimidine (1-10) compounds were prepared via traditional cycloaddition and condensation method. The compounds tetrazolo [1,5-a]pyrimidine (11 a,12 a, and 13 a), azido-(1H-tetrazol-1-yl) pyrimidine (14 a and 15 a) and tetrazolo[1,5-c]pyrimidine (16 a) were synthesized by simultaneously introducing conventional and nucleophilic substitution approaches. The latter technique was easy to process and reduce the synthesis time. The factors (solvent, temperature, steric effect, electron-donating groups, and electron-withdrawing groups) were found responsible for steering the azido-tetrazole equilibrium in the compounds 11 a, 12 a, 13 a, and 16 a. All the prepared compounds were well characterized including single-crystal X-ray diffraction struc- tures of 1, 3, 4, 6, 8, 10, 11 a, 12 a, 13 a, 14 a, 15 a, and 16 a. Thermal behaviour was investigated by differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). The current work is significant to the development of a new class of pyrimidine modified tetrazole and azido derivatives in sense of easy reaction approach, good to excellent yields, safe process, and simple work-ups.

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Section: Resultsmentioning

confidence: 86%

“…Scheme shows the two‐step synthesis of compounds 12 a , 15 a , and 16 a with the common initial conversion of chloro to azido group via nucleophilic S N 2 substitution reaction . Whereas, in the second step, each entry follows the different synthesis routes.…”

Section: Resultsmentioning

confidence: 99%

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

et al. 2020

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“…Commercial reagents were used without purification. Compound 2 was obtained by a known method [8,9]. [1,5-a]Quinazoline (5a) 1-octylamine (0.60 g, 0.77 mL, 4.7 mmol) was added to a solution of 2,4-diazidoquinazoline (2) (0.20 g, 0.94 mmol) in a mixture of DMF (0.5 mL) and water (1 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Previously [8] we reported that nucleophilic aromatic substitutions of 2,4-diazidoquinazoline (2) with amines, such as piperidine, morpholine and pyrrolidine, proceed with high C(4) selectivity (or C(5) selectivity in respect to tetrazolo-form 3). For the first time the molecular structure of 5-(piperidin-1-yl)tetrazolo [1,5-a]quinazoline was proved by X-ray diffraction…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Alkylamino-2-Triazolylquinazolines

Goliškina¹,

Cīrule²,

Bizdēna³

et al. 2017

Materials Science and Applied Chemistry

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“…Our group has developed several synthetic methodologies that make use of azidoquinazoline, 37 azidopurine, 38 and azido-7-deazapurine 39 derivatives as versatile starting materials. We have extended various S N Ar approaches involving azido group as a leaving group.…”

mentioning

confidence: 99%

Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines

et al. 2020

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Nucleophilic 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 crystallography. The latter exist in tautomeric equilibrium with their 2-azidoquinazoline form, which provides possibility for copper-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction, leading to the 4-alkyl/arylthio-2-(1H-1,2,3-triazol-1-yl)quinazolines.

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Structural Proof of Tetrazolo[1,5-a]quinazoline Derivatives and their Application in the Synthesis of 4-Amino-2-(1,2,3-triazol-1-yl)quinazolines*

Cited by 13 publications

References 17 publications

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

Synthesis of 4-Alkylamino-2-Triazolylquinazolines

Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines

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