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
- Authors: Remizov Y.O.1, Pevzner L.M.1, Petrov M.L.1
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Affiliations:
- St. Petersburg State Institute of Technology (Technical University)
- Issue: Vol 88, No 7 (2018)
- Pages: 1402-1410
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222310
- DOI: https://doi.org/10.1134/S1070363218070095
- ID: 222310
Cite item
Abstract
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.
About the authors
Yu. O. Remizov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190031
L. M. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190031
M. L. Petrov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190031