Quinolone analogs 16: A facile D-H exchange for 3-h proton of 2-substituted 4-quinolones in acidic media

Yoshihisa Kurasawa, Kiminari Yoshida, Naoki Yamazaki, Kenji Sasaki, Yoshito Zamami, Zhao Min, Atsumi Togi, Hideyuki Ito, Eisuke Kaji, Haruhiko Fukaya

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Abstract

The 4-quinolones having the urea or carbamate moiety at the 2-position showed the facile deuterium-hydrogen (D-H) exchange of the 3-H proton in deuteriotrifluoroacetic acid-deuteriodimethyl sulfoxide (3:1) at 60°C, whereas the 4-quinolones possessing the carboxylate or carbohydrazide group at the 2-position and 2-substituted 4-methoxyquinolines represented no D-H exchange of the 3-H proton under the same condition. The aforementioned D-H exchange was found to require both the tautomerization of the 4-quinolone into 4-hydroxyquinoline in strongly acidic media and the nitrogen functional group at the 2-position.

Original languageEnglish
Pages (from-to)1821-1829
Number of pages9
JournalJournal of Heterocyclic Chemistry
Volume51
Issue number6
DOIs
Publication statusPublished - Nov 2014

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kurasawa, Y., Yoshida, K., Yamazaki, N., Sasaki, K., Zamami, Y., Min, Z., Togi, A., Ito, H., Kaji, E., & Fukaya, H. (2014). Quinolone analogs 16: A facile D-H exchange for 3-h proton of 2-substituted 4-quinolones in acidic media. Journal of Heterocyclic Chemistry, 51(6), 1821-1829. https://doi.org/10.1002/jhet.1933