Michael Addition–Aromatization Reaction of Dienylimines Bearing a Leaving Group and Its Application to the Preparation of Thiol-Selective Labeling Reagents Capable of Forming Strong Carbon–Sulfur Bonds

The reaction of a dienylimine with thiols was found to proceed smoothly to afford the corresponding indolines bearing aromatic carbon–sulfur bonds as a result of a Michael addition–aromatization sequence. Furthermore, this reaction was applied to the development of fluorogenic dienylimines that coul...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (22), p.11433-11443
Main Authors: Miyoshi, Tetsuya, Aoki, Yuka, Uno, Yumina, Araki, Mina, Kamatani, Takahiro, Fujii, Daichi, Fujita, Yoshinori, Takeda, Norihiko, Ueda, Masafumi, Kitagawa, Hiroshi, Emoto, Noriaki, Mukai, Takahiro, Tanaka, Masafumi, Miyata, Okiko
Format: Article
Language:English
Subjects:
Carbon - chemistry
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Imines - chemistry
Molecular Conformation
Sulfhydryl Compounds - chemistry
Sulfur - chemistry
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Summary:The reaction of a dienylimine with thiols was found to proceed smoothly to afford the corresponding indolines bearing aromatic carbon–sulfur bonds as a result of a Michael addition–aromatization sequence. Furthermore, this reaction was applied to the development of fluorogenic dienylimines that could be used as thiol-selective fluorescent labeling reagents.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402002k