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Synthesis of New 4-Vinyl-1,2,3-Thiadiazoles

Journal Article


Abstract


  • Simple and convenient methods for the synthesis of a range of new 1,2,3-thiadiazole derivatives, including ethyl esters, alcohols, and aldehydes, were developed. Moreover, twenty-nine new structurally diverse 4-vinyl-1,2,3-thiadiazoles were successfully synthesized in 18–89 % yield via Knoevenagel condensation. NOESY-experiments were performed for E/Z-assignment of isomeric mixtures. The structure of five of the new vinylic derivatives has been confirmed using X-ray diffraction analysis. Using the example of ethyl (E)-2-cyano-3-(5-(pyrrolidin-1-yl)-1,2,3-thiadiazol-4-yl)acrylate, the possibility of dimerization with the formation of diethyl(1R,2R,3S,4S)-1,3-dicyano-2,4-bis(5-(pyrrolidin-1-yl)-1,2,3-thiadiazol-4-yl)cyclobutane-1,3-dicarboxylate was demonstrated, allowing the first 1,2,3-thiadiazole substituted cyclobutane to be synthesized.

Publication Date


  • 2021

Citation


  • Tokareva, M. A., Keaveney, S. T., Pernik, I., Messerle, B. A., & Glukhareva, T. V. (2021). Synthesis of New 4-Vinyl-1,2,3-Thiadiazoles. ChemistrySelect, 6(39), 10527-10531. doi:10.1002/slct.202102760

Scopus Eid


  • 2-s2.0-85117362438

Start Page


  • 10527

End Page


  • 10531

Volume


  • 6

Issue


  • 39

Abstract


  • Simple and convenient methods for the synthesis of a range of new 1,2,3-thiadiazole derivatives, including ethyl esters, alcohols, and aldehydes, were developed. Moreover, twenty-nine new structurally diverse 4-vinyl-1,2,3-thiadiazoles were successfully synthesized in 18–89 % yield via Knoevenagel condensation. NOESY-experiments were performed for E/Z-assignment of isomeric mixtures. The structure of five of the new vinylic derivatives has been confirmed using X-ray diffraction analysis. Using the example of ethyl (E)-2-cyano-3-(5-(pyrrolidin-1-yl)-1,2,3-thiadiazol-4-yl)acrylate, the possibility of dimerization with the formation of diethyl(1R,2R,3S,4S)-1,3-dicyano-2,4-bis(5-(pyrrolidin-1-yl)-1,2,3-thiadiazol-4-yl)cyclobutane-1,3-dicarboxylate was demonstrated, allowing the first 1,2,3-thiadiazole substituted cyclobutane to be synthesized.

Publication Date


  • 2021

Citation


  • Tokareva, M. A., Keaveney, S. T., Pernik, I., Messerle, B. A., & Glukhareva, T. V. (2021). Synthesis of New 4-Vinyl-1,2,3-Thiadiazoles. ChemistrySelect, 6(39), 10527-10531. doi:10.1002/slct.202102760

Scopus Eid


  • 2-s2.0-85117362438

Start Page


  • 10527

End Page


  • 10531

Volume


  • 6

Issue


  • 39