Experimental and computational study of intermolecular migration of N,N-dimethylcarbamoyl group from N(7) to N(1) on a 7-azaindoline derivative

Autor:	Norio Fujiwara, Yoshiharu Uruno, Shinya Usui, Atsushi Suwa, Akio Tanaka, Kazuki Hashimoto, Kentaro Takai, Wataru Katoda, Yasuko Konishi, Takaaki Sumiyoshi, Yasunao Inoue
Rok vydání:	2013
Předmět:	Reaction conditions Reaction mechanism Stereochemistry Organic Chemistry Intermolecular force Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Nitrogen atom Group (periodic table) Yield (chemistry) Drug Discovery Derivative (chemistry)
Zdroj:	Tetrahedron. 69:9675-9681
ISSN:	0040-4020
Popis:	N , N -Dimethylcarbamoylation of the anilinic nitrogen atom N(1) on the spiro 7-azaindoline consists of two steps. The first step is N , N -dimethylcarbamoylation of the pyridyl nitrogen atom N(7), leading to the formation of an isolable intermediate. The second step is intermolecular migration of the N , N -dimethylcarbamoyl group from the pyridyl nitrogen atom N(7) to the anilinic nitrogen atom N(1). We accomplished optimization of the reaction conditions based on the revealed reaction mechanism and a large scale synthesis of compound 3 in quantitative yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::28cfdcc779cdfb6f31d9d5d853a53a73 https://doi.org/10.1016/j.tet.2013.09.024 Zobrazit plný text záznamu Full Text from ScienceDirect