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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 - 2014

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4-Quinolones
Deuterium
Quinolones
Protons
Hydrogen
sulfoxide
Carbamates
Functional groups
Urea
Nitrogen
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Quinolone analogs 16 : A facile D-H exchange for 3-h proton of 2-substituted 4-quinolones in acidic media. / Kurasawa, Yoshihisa; Yoshida, Kiminari; Yamazaki, Naoki; Sasaki, Kenji; Zamami, Yoshito; Min, Zhao; Togi, Atsumi; Ito, Hideyuki; Kaji, Eisuke; Fukaya, Haruhiko.

In: Journal of Heterocyclic Chemistry, Vol. 51, No. 6, 2014, p. 1821-1829.

Research output: Contribution to journalArticle

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, vol. 51, no. 6, pp. 1821-1829. https://doi.org/10.1002/jhet.1933
Kurasawa, Yoshihisa ; Yoshida, Kiminari ; Yamazaki, Naoki ; Sasaki, Kenji ; Zamami, Yoshito ; Min, Zhao ; Togi, Atsumi ; Ito, Hideyuki ; Kaji, Eisuke ; Fukaya, Haruhiko. / Quinolone analogs 16 : A facile D-H exchange for 3-h proton of 2-substituted 4-quinolones in acidic media. In: Journal of Heterocyclic Chemistry. 2014 ; Vol. 51, No. 6. pp. 1821-1829.
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AU - Sasaki, Kenji

AU - Zamami, Yoshito

AU - Min, Zhao

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AU - Fukaya, Haruhiko

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