Synthesis of the Derivatives of 4-(5-Aryl-3-methylfuran-3-yl)-1,2,3-thiadiazole and Functionalization of 5-Aryl-2- methylfuran via Reactions of Thiadiazole Ring
- Авторы: Remizov Y.1, Pevzner L.1, Petrov M.1
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Учреждения:
- St. Petersburg State Institute of Technology (Technical University)
- Выпуск: Том 88, № 7 (2018)
- Страницы: 1402-1410
- Раздел: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222310
- DOI: https://doi.org/10.1134/S1070363218070095
- ID: 222310
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Аннотация
By arylation of 2-methyl-3-acetylfuran via the Gomberg–Bachmann reaction 5-(4-ethoxycarbonylphenyl)-, 5-(2-nitrophenyl), and 5-(4-nitrophenyl)-2-methyl-3-acetylfurans were synthesized. Carboethoxyhydrazones of 2-methyl-5-phenyl-3-acetylfuran and its phenyl-substituted analogs when treated with thionyl chloride form 4-(5-aryl-2-methylfuran-3-yl)-1,2,3-thiadiazoles by the Hurd–Mori reaction. Thermal stability of obtained compounds increases with the increase in electron-acceptor action of substituent in phenyl ring. Opening of thidiazole ring in the compounds synthesized under the action of potassium tert-butylate in THF in the presence of alkyl iodides leads to the corresponding alkylthioethynylfurans. Performing the reaction with potassium carbonate in DMF in the presence of excess morpholine permits the preparation of (2-methyl-5- arylfuran-3-yl)thioacetylmorpholides.
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Об авторах
Yu. Remizov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Россия, Moskovskii pr. 26, St. Petersburg, 190031
L. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Автор, ответственный за переписку.
Email: pevzner_lm@list.ru
Россия, Moskovskii pr. 26, St. Petersburg, 190031
M. Petrov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Россия, Moskovskii pr. 26, St. Petersburg, 190031