Synlett 2018; 29(13): 1711-1716
DOI: 10.1055/s-0037-1610187
letter
© Georg Thieme Verlag Stuttgart · New York

A Unique Skeletal Rearrangement of a Bicyclo[3.3.1]nonanetrione to a Tetrahydroquinolin-2(1H)-one System

Qi Shen
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Fang Liu
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: yongliang@nju.edu.cn
,
Yu-Chao Zhang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Jie Wang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Lei Zhang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Yue Wang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Hong-Xi Xu
c   School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P. R. of China
,
Zhuzhou Shao
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: yongliang@nju.edu.cn
,
Yang Cao
d   Institute of New Energy, Shenzhen 518031, P. R. of China
,
Jing Wu*
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
,
Yong Liang*
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: yongliang@nju.edu.cn
,
Jian-Xin Li*
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   eMail: wujnju@nju.edu.cn   eMail: lijxnju@nju.edu.cn
› Institutsangaben

This work was supported by National Natural Science Foundation of China (21702101, 21778029, and 21761142001) and the Fundamental Research Funds for the Central Universities in China. Y.L. thanks the ­National Thousand Young Talents Program, Jiangsu Specially­Appointed Professor Plan, and the NSF of Jiangsu Province (BK20170631) in China for financial support. Y.C. acknowledges the support from the Shenzhen Peacock Plan (No.1208040050847074).
Weitere Informationen

Publikationsverlauf

Received: 06. April 2018

Accepted after revision: 27. Mai 2018

Publikationsdatum:
02. Juli 2018 (online)


Preview

Abstract

The unexpected formation of a 4-hydroxytetrahydroquinolin-2(1H)-one from a bicyclo[3.3.1]nonanetrione system and an amino alcohol in the presence of TsOH is reported. The mechanism of this transformation was studied by DFT calculations. The reaction provides an entry to the synthesis of highly functionalized 4-hydroxytetrahydroquinolin-2(1H)-ones.

Supporting Information