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

doi:10.1002/jhet.1933

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

University Hospital

Research output: Contribution to journal › Article › peer-review

3 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 language	English
Pages (from-to)	1821-1829
Number of pages	9
Journal	Journal of Heterocyclic Chemistry
Volume	51
Issue number	6
DOIs	https://doi.org/10.1002/jhet.1933
Publication status	Published - Nov 2014

ASJC Scopus subject areas

Organic Chemistry

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

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.",

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

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doi = "10.1002/jhet.1933",

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volume = "51",

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T1 - Quinolone analogs 16

T2 - A facile D-H exchange for 3-h proton of 2-substituted 4-quinolones in acidic media

AU - Kurasawa, Yoshihisa

AU - Yoshida, Kiminari

AU - Yamazaki, Naoki

AU - Sasaki, Kenji

AU - Zamami, Yoshito

AU - Min, Zhao

AU - Togi, Atsumi

AU - Ito, Hideyuki

AU - Kaji, Eisuke

AU - Fukaya, Haruhiko

PY - 2014/11

Y1 - 2014/11

N2 - 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.

AB - 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.

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

Abstract

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