Tetrahedron

Synthesis of 4-and 6-substituted nitroindoles

N Moskalev, M Barbasiewicz, M Mąkosza

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

Full Text: HTML

Citation Number: 33

Abstract

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 ...

Related Articles:

Ketone synthesis via palladium-catalyzed carbonylation of organoaluminium compounds

[Bumagin, N. A.; Ponomaryov, A. B.; Beletskaya, I. P. Tetrahedron Letters, 1985 , vol. 26, # 39 p. 4819 - 4822]

Synthesis of novel substituted diaryl-1, 4-diazepines

[Ramajayam; Giridhar, Rajani; Yadav Chemistry of Heterocyclic Compounds, 2006 , vol. 42, # 7 p. 901 - 906]

KO t Bu-Mediated Aerobic Transition-Metal-Free Regioselective β-Arylation of Indoles: Synthesis of β-(2-/4-Nitroaryl)-indoles

[Xu, Qing-Long; Gao, Hongyin; Yousufuddin, Muhammed; Ess, Daniel H.; Kuerti, Laszlo Journal of the American Chemical Society, 2013 , vol. 135, # 38 p. 14048 - 14051]

A novel nucleophilic substitution of the formyl group in p-nitrobenzaldehyde with some carbanions

[Iwasaki, Genji; Saeki, Seitaro; Hamana, Masatomo Chemistry Letters, 1986 , p. 173 - 176]

An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal S RN 1 reactions

[Soria-Castro, Silvia M.; Caminos, Daniel A.; Penenory, Alicia B. RSC Advances, 2014 , vol. 4, # 34 p. 17490 - 17497]

More Articles...