A Unique Skeletal Rearrangement of a Bicyclo[3.3.1]nonanetrione to a Tetrahydroquinolin-2(1H)-one System-Reference-Cited by-同舟云学术

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

Published:2018-07-02 Issue:13 Volume:29 Page:1711-1716
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Wu Jing¹,Liang Yong²,Li Jian-Xin¹,Shen Qi¹,Liu Fang²,Zhang Yu-Chao¹,Wang Jie¹,Zhang Lei¹,Wang Yue¹,Xu Hong-Xi³,Shao Zhuzhou²,Cao Yang⁴

Affiliation:

1. 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

2. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University

3. School of Pharmacy, Shanghai University of Traditional Chinese Medicine

4. Institute of New Energy

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.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610187.pdf

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