Synthesis 2015; 47(15): 2270-2280
DOI: 10.1055/s-0034-1380657
paper
© Georg Thieme Verlag Stuttgart · New York

Selective Oxidation of 1-Tetralones to 1,2-Naphthoquinones with IBX and to 1,4-Naphthoquinones with Oxone® and 2-Iodobenzoic Acid

Jiangmeng Ren
a   Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, Shanghai 200237, P. R. of China
,
Lei Lu
a   Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, Shanghai 200237, P. R. of China
b   Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, P. R. of China
,
Junchao Xu
a   Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, Shanghai 200237, P. R. of China
b   Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, P. R. of China
,
Tianyin Yu
a   Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, Shanghai 200237, P. R. of China
b   Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, P. R. of China
,
Bu-Bing Zeng*
a   Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, Shanghai 200237, P. R. of China
b   Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, P. R. of China
c   Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: zengbb@ecust.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 21 January 2015

Accepted after revision: 26 March 2015

Publication Date:
07 May 2015 (online)


Abstract

The preparation of naphthoquinones by oxidation of 1-tetralone derivatives is reported. 1,2-Naphthoquinones were prepared by oxidation with IBX and 1,4-naphthoquinones were prepared by oxidation using Oxone® and 2-iodobenzoic acid. The mechanistic pathways are also discussed.

Supporting Information

 
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