Unusual O-Alkylation of 2-Hydroxy-1,4-naphthoquinone Utilizing Alkoxymethyl Chlorides

Tokutaro Ogata; Tomoyo Yoshida; Manami Tanaka; Chie Fukuhara; Maki Shimizu; Junko Ishii; Arisa Nishiuchi; Kiyofumi Inamoto; Tetsutaro Kimachi

doi:10.1248/cpb.c15-00220

Communication to the Editor

Unusual O-Alkylation of 2-Hydroxy-1,4-naphthoquinone Utilizing Alkoxymethyl Chlorides

Tokutaro Ogata , Tomoyo Yoshida, Manami Tanaka, Chie Fukuhara, Maki Shimizu, Junko Ishii, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi

Author information

Tokutaro Ogata Corresponding author
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Tomoyo Yoshida
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Manami Tanaka
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Chie Fukuhara
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Maki Shimizu
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Junko Ishii
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Arisa Nishiuchi
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Kiyofumi Inamoto
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University
Tetsutaro Kimachi
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University

Keywords: naphthoquinone, protecting group, hydride, alkylation, heterocycle

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2015 Volume 63 Issue 7 Pages 485-488

DOI https://doi.org/10.1248/cpb.c15-00220

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Abstract

A new type of O-alkylation of 2-hydroxy-1,4-naphthoquinone with alkoxymethyl chlorides is described. The reaction course can be controlled by the choice of base and yields O-alkylated or O-alkoxymethylated products in high yield with high selectivity.

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