A novel method of indole ring system construction: One-pot synthesis of 4-and 6-nitroindole derivatives via base promoted reaction between 3-nitroaniline and ketones

Authors
Moskalev, N Makosza, M
Citation
N. Moskalev et M. Makosza, A novel method of indole ring system construction: One-pot synthesis of 4-and 6-nitroindole derivatives via base promoted reaction between 3-nitroaniline and ketones, TETRAHEDR L, 40(29), 1999, pp. 5395-5398
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5395 - 5398
Database
ISI
SICI code
0040-4039(19990716)40:29<5395:ANMOIR>2.0.ZU;2-6
Abstract
Base promoted condensation of ketones RCQCH(2)R' with 3-nitroaniline result s in formation of the corresponding 4- and 6-nitro-2-R-3-R'-indoles. This m ultistep process apparently includes oxidative nucleophilic substitution of hydrogen in the aromatic ring of the aniline by the enolate anion and subs equent cyclization of the so formed ortho-aminoketone intermediate to indol es via a Baeyer type reaction. (C) 1999 Elsevier Science Ltd. All rights re served.