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Paper | Special issue | Vol 103, No. 1, 2021, pp.416-424
Published online, 29th October, 2020
DOI: 10.3987/COM-20-S(K)28
Synthesis of 1-Methoxy-1H-indoles with a Heterocyclic Moiety via Unstable Indole Isothiocyanate by Using Enzyme from Brassicaceae Plant

Kaori Ryu, Seikou Nakamura,* Koya Miyagawa, Souichi Nakashima, and Hisashi Matsuda*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

A synthesis of five 1-methoxy-1H-indole derivatives with imidazole, pyrazole, 1H-1,2,3-triazole, and 1H-1,2,4-triazole moieties was achieved by focusing on the formation mechanism of plant constituents. The objective 1-methoxy-1H-indole derivatives were obtained in situ (in one step) through the reaction of an unstable 3-(isothiocyanatomethyl)-1-methoxy-1H-indole, which was derived from neoglucobrassicin and plant enzyme myrosinase, and a heterocyclic compound. We have great hopes that this method would be useful for the development of medicinal seeds.