Nucleophilic substitution reaction of 1-methoxy-6-nitro-indole

金沢大学大学院自然科学研究科生理活性物質科学金沢大学薬学部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-methylthiomethytyl-6-nitroindole and its 2-methylthio derivative, and diethyl 2-(6-nitroindol-3-yl)methylmalonate, respectively. Possible reaction mechanism is discussed