sym-triazine derivatives. 9. Reaction of sym-triazines containing trichloromethyl and ethoxycarbonyl groups with phenylhydrazine

Алексеева, Н. В.; Turchin, K. F.; Анисимова, О. С.; Sheinker, Yu. N.; Yakhontov, L. N.

doi:10.1007/bf00473967

Cited by 2 publications

(8 citation statements)

References 4 publications

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“…Показано, что данное превращение является региоселективным и легко происходит при кипячении исходных соединений в уксусной кислоте или пропаноле-2 с образованием 2-арил-5-трихлорметил-5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолинов. Предложен и обоснован возможный механизм формирования 5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолинов, который представляет собой тандемное превращение, которое включает A N E и A N процессы. Полученный 2-фенил-5трихлорометил-5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолин был исследован в реакциях с N-нуклеофилами.…”

unclassified

“…Предложен и обоснован возможный механизм формирования 5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолинов, который представляет собой тандемное превращение, которое включает A N E и A N процессы. Полученный 2-фенил-5трихлорометил-5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолин был исследован в реакциях с N-нуклеофилами. Показано, что упомянутая выше реакция вне зависимости от природы нуклеофила приводит к образованию 2-фенил-5-(дихлорметил)- [1,2,4]триазоло [1,5-c]хиназолина.…”

unclassified

“…Полученный 2-фенил-5трихлорометил-5,6-дигидро- [1,2,4]триазоло [1,5-с]хиназолин был исследован в реакциях с N-нуклеофилами. Показано, что упомянутая выше реакция вне зависимости от природы нуклеофила приводит к образованию 2-фенил-5-(дихлорметил)- [1,2,4]триазоло [1,5-c]хиназолина. Представлен механизм упомянутого превращения, который представляет собой последовательность β-элиминирования по Е 1cb-механизму изомеризации.…”

unclassified

“…Показано, что для 2-арил-5-трихлорметил-5,6дигидро-[1,2,4]триазоло [1,5-с]хиназолинов характеристическими являются сигналы атома углерода положения 5 при 79.25-77.95 м.д., в то время как ароматизация ведет к его дезэкранированию (163.41 м.д.). Показана перспективность дальнейшей химической модификации 2-арил-5-(дихлорметил)- [1,2,4]триазоло [1,5-c]хиназолинов.…”

unclassified

“…Characteristics of chemical transformations of compounds with the trichloromethyl moiety in heterocyclic fragments were widely discussed in recent publication. The authors described the features of their interaction with N-, О-nucleophiles by S NAr -or tele-S N -mechanisms and formation of the corresponding N-, O-substituted heterocyclic fragments [1][2][3]. In order to expand the synthetic potential of the reaction mentioned above it would be interesting to study the interaction of non-aromatic heterocyclic compounds with trichloromethyl substituent at sp 3 hybridized carbon atom.…”

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5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines. Message 3. Synthesis of 2-aryl-5-trichloromethyl-5,6-dihydro[1,2,4]triazolo[1,5-с]quinazolines and their reactivity towards n-nucleophiles

Kholodnyak

Voskoboynik

Коваленко

et al. 2016

J. org. pharm. chem.

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quinazolines formation as result of [5+1]-cyclocondensation of the corresponding [2-(3-aryl-1H-1,2,4-triazole-5-yl)phenyl]amines with chloral hydrate are described in the article. It has been shown that this transformation is regioselective, occurs by refluxing of the initial compounds in acetic acid with formation of 2-aryl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines. The possible mechanism of 5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines has been proposed and substantiated. It has been shown that the reaction proceeds as step-by-step transformation that includes A N E and A N processes. The 2-phenyl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazoline obtained was studied in reactions with N-nucleophiles. It has been found that regardless of the nature of nucleophile the reaction mentioned above leads to formation of 2-phenyl-5-(dichloromethyl)-[1,2,4]triazolo[1,5-c]qinazoline. The mechanism of the transformation mentioned above is given; it is β-elimination on the Е 1cb-mechanism followed by isomerisation. The structure of the compounds synthesized has been confirmed by the complex of physicochemical methods, including 1 H-, 13 C-NMR-spectrometry, chromato-massspectrometry, mass-spectrometry and X-ray structural study. A detailed analysis of 1 H and 13 C-NMR spectral data of the compounds synthesized has been conducted. It has been found that the signals of the carbon atom in position 5 at 79.25-77.95 ppm were characteristic for 2-aryl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines, whereas aromatization of the molecule leads to significant deshielding of this carbon atom (163.41 ppm). The prospects of further chemical modification of 2-aryl-5-(dichloromethyl)-[1,2,4]triazolo[1,5-c]quinazolines has been discussed.

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confidence: 99%

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5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines. Message 3. Synthesis of 2-aryl-5-trichloromethyl-5,6-dihydro[1,2,4]triazolo[1,5-с]quinazolines and their reactivity towards n-nucleophiles

Kholodnyak

Voskoboynik

Коваленко

et al. 2016

J. org. pharm. chem.

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Synthesis of 6-chloro(dichloro-, trichloro-)-methyl-3-R-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]- quinazolin-2-ones and their modification in reactions with nucleophilic and non-nucleophilic bases

Grytsak¹,

Moskalenko²,

Voskoboynik³

et al. 2021

Vopr. Khim. Khim. Tekhnol.

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The synthesis of 6-chloro-(dichloro-, trichloro)methyl-3-R-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-ones and their modification under the action of nucleophilic and/or basic reagents are described in this article. It was shown that 6-chloro-(dichloro-, trichloro)methyl-3-R-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-ones can be prepared by cyclocondensation of 3-(aminophenyl)-6-R-1,2;4-triazine-5(2Н)-ones with chloro-(dichloro-)acetaldehyde or chloral hydrate. The reactivity of the synthesized compounds toward nucleophilic base morpholine and non-nucleophilic base diisopropylethylamine (DIPEA) under different conditions was studied. It was shown that the prepared compounds under the action of morpholine and/or DIPEA can be converted into the products of substitution, elimination or elimination followed by isomerization and substitution. Refluxing of 6-(chloromethyl)-3-R-6,7-dihydro-2Н-[1,2,4]triazino[2,3-с]quinazoline-2-ones with equimolar quantity of morpholine and 10% excess of DIPEA in ethylene glycol monoethyl ether (EGEE) yielded the products on N-alkylation. 6-(Morpholinomethyl)-3-R-2H-[1,2,4]triazino[2,3-с]quinazoline-2-ones were obtained by heating of 6-dichloromethyl-3-R-6,7-dihydro-2Н-[1,2,4]triazino[2,3-с]quinazoline-2-ones with five-fold excess of morpholine in EGEE. Reaction of 3-R-6-(trichloromethyl)-6,7-dihydro-2H-[1,2,4]triazino[2,3-с]quinazolin-2-ones with three-fold excess of DIPEA in EGEE yielded 3-R-2Н-[1,2,4]triazino[2,3-с]quinazoline-2-ones. The physicochemical and spectral characteristics of the prepared compounds were determined and discussed.

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sym-triazine derivatives. 9. Reaction of sym-triazines containing trichloromethyl and ethoxycarbonyl groups with phenylhydrazine

Cited by 2 publications

References 4 publications

5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines. Message 3. Synthesis of 2-aryl-5-trichloromethyl-5,6-dihydro[1,2,4]triazolo[1,5-с]quinazolines and their reactivity towards n-nucleophiles

5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines. Message 3. Synthesis of 2-aryl-5-trichloromethyl-5,6-dihydro[1,2,4]triazolo[1,5-с]quinazolines and their reactivity towards n-nucleophiles

Synthesis of 6-chloro(dichloro-, trichloro-)-methyl-3-R-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]- quinazolin-2-ones and their modification in reactions with nucleophilic and non-nucleophilic bases

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