Tetrahedron

Synthesis of 4-and 6-substituted nitroindoles

N Moskalev, M Barbasiewicz, M Mąkosza

文献索引：Moskalev, Nikolai; Barbasiewicz, Michal; Makosza, Mieczyslaw Tetrahedron, 2004 , vol. 60, # 2 p. 347 - 358

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被引用次数: 33

摘要

Enolizable ketones react with m-nitroaniline in the presence of strong base such as t-BuOK to give 4-and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic σH adducts that are additionally stabilized by intramolecular interaction between the amino and the carbonyl group. Spontaneous oxidation of the σH adducts ...