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Note | Regular issue | Vol 55, No. 6, 2001, pp.1151-1159
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9198
Nucleophilic Substitution Reaction of 1-Methoxy-6-nitroindole

Koji Yamada, Toshiya Kawasaki, Tomomi Fujita, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Nucleophilic substitution reaction of 1-methoxy-6-nitroindole (1) was examined. In the reaction with sodium methoxide or sodium cyanide as a nucleophile, 2- and 3-methoxy-6-nitroindoles, and 7-cyano-6-nitroindole were obtained, respectively. A novel methylene homologation at the 3-position was found in the reaction of 1 with sodium methyl sulfide or potassium salt of diethyl malonate to give 3-methylthiomethyl-6-nitroindole and its 2-methylthio derivative, and diethyl 2-(6-nitroindol-3-yl)methylmalonate, respectively. Possible reaction mechanism is discussed.