Citation: Zhiguo Zhang, Xiyang Cao, Xiaoqing Song, Gang Wang, Bingbing Shi, Xiang Li, Nana Ma, Lantao Liu, Guisheng Zhang. Metal-free nucleophilic 7, 8-dearomatization of quinolines: Spiroannulation of aminoquinoline protected amino acids[J]. Chinese Chemical Letters, ;2023, 34(2): 107779. doi: 10.1016/j.cclet.2022.107779 shu

Metal-free nucleophilic 7, 8-dearomatization of quinolines: Spiroannulation of aminoquinoline protected amino acids

Zhiguo Zhang ^{a, *,} ,
Xiyang Cao ^a ,
Xiaoqing Song ^a ,
Gang Wang ^a ,
Bingbing Shi ^a ,
Xiang Li ^a ,
Nana Ma ^{a, *,} ,
Lantao Liu ^b ,
Guisheng Zhang ^{a, *,}

a.
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
b.
The College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China

zhangzg@htu.edu.cn

mann076@htu.edu.cn

zgs6668@yahoo.com

Received Date: 26 May 2022
Revised Date: 19 August 2022
Accepted Date: 23 August 2022
Available Online: 26 August 2022

Figures(8)

Atom- and step-economy in IBX assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary α-amino acid analogs offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocenter in 20%–91% yields under mild conditions via 7, 8-dearomatization of quinolines. Free of a preinstalled activation group is highlight of this intramolecular oxidation spiroannulation tandem reaction. This type of N-heterospirocycles, traditionally difficult to access, may open the door to a potentially interest scaffold for synthetic and medicinal chemistry.
- Dearomatization,
- Spiroannulation,
- Aminoquinoline,
- Amino acids,
- Hypervalent iodine reagents
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