A novel simple method of synthesis of 2-amino-4-(-6-) nitroindoles via base promoted condensation of m-nitroanilines with nitriles

Authors
Moskalev, N Makosza, M
Citation
N. Moskalev et M. Makosza, A novel simple method of synthesis of 2-amino-4-(-6-) nitroindoles via base promoted condensation of m-nitroanilines with nitriles, HETEROCYCLE, 52(2), 2000, pp. 533-536
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
2
Year of publication
2000
Pages
533 - 536
Database
ISI
SICI code
0385-5414(20000201)52:2<533:ANSMOS>2.0.ZU;2-C
Abstract
Base promoted condensation of nitriles (RCH2CN) with m-nitroanilines at roo m temperature results in the formation of 3-alkyl- or 3-aryl-2-amino-4-(-6- ) nitroindoles. This multistep process includes presumably nucleophilic sub stitution of hydrogen (or halogen) in the nitroaromatic ring by the nitrile carbanion and subsequent cyclization of the ortho-aminophenylacetonitriles so formed to give the aminoindoles.