文献类型：期刊文献

英文题名：Metal-Free Intramolecular [3+2] Cycloaddition of γ-Hydroxy Acetylenic Ketones with Alkynes for the Synthesis of Naphtho[1,2-c]furan-5-ones and Its Derivatization via a Selective C(sp²)-H Deuteration Reaction

作者：Ning, Si-Si[1];Meng, Dan[1];Zhang, Jie-Yun[1];Liu, Shi-Lei[1];Zhou, Ni-Ni[1];Jin, Xiaojie[2];Zhu, Hai-Tao[1]

第一作者：Ning, Si-Si

通信作者：Zhu, HT[1]

机构：[1]Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shannxi Key Lab Phytochem, Baoji 721013, Peoples R China;[2]Gansu Univ Chinese Med, Key Lab Mol Med & Chinese Med Prevent & Treatment, Lanzhou 730000, Peoples R China

第一机构：Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shannxi Key Lab Phytochem, Baoji 721013, Peoples R China

通信机构：[1]corresponding author), Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shannxi Key Lab Phytochem, Baoji 721013, Peoples R China.

年份：2021

卷号：86

期号：11

起止页码：7347

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000661138500004)，CCR-EXPANDED(收录号:WOS:000661138500004)】；

基金：The authors gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (21702006), the Fund of the Rising Stars of Shanxi Province (2019KJXX-001), the Education Department of Shaanxi Province Key Laboratory Project (19JS005), the Ph.D. scientific research projects of Baoji University of Arts and Sciences (ZK16060), and the Graduate Innovative Research Projects of Baoji University of Arts and Sciences (YJSCX19YB01). The authors are grateful to Dr. Xiaojie Jin (Gansu University of Chinese Medicine) for help with the DFT calculations.

语种：英文

摘要：A metal-free intramolecular [3+2] cycloaddtion has been achieved by treating benzene-linked propynol-ynes with AcOH/H2O in a one-pot manner. The reaction provides greener, 100% atom-economic, highly regioselective, and more practical access to functionalized naphtho[1,2-c]furan-5-ones with valuable and versatile applications. The regioselective alpha-deuteration of naphtho[1,2-c]furan-5-ones has been also presented with excellent deuterium incorporation and chemical yields. Moreover, the fluorescent properties of naphtho[1,2-c]furan-5-one products have been investigated in solution.