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Synlett 2018; 29(13): 1711-1716
DOI: 10.1055/s-0037-1610187
DOI: 10.1055/s-0037-1610187
letter
A Unique Skeletal Rearrangement of a Bicyclo[3.3.1]nonanetrione to a Tetrahydroquinolin-2(1H)-one System
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).Further Information
Publication History
Received: 06 April 2018
Accepted after revision: 27 May 2018
Publication Date:
02 July 2018 (online)
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.
Key words
polyprenylated acylphloroglucinols - skeletal rearrangement - tetrahydroquinolinones - density functional theory - bicyclononanetriones - tetrahydroquinolinonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610187.
- Supporting Information
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