22980-05-8Relevant academic research and scientific papers
Nucleophilic substitution reaction of 1-methoxy-6-nitro-indole
Yamada, Koji,Kawasaki, Toshiya,Fujita, Tomomi,Somei, Masanori
, p. 1151 - 1159 (2007/10/03)
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.
