Reaction of o-iodoaniline with aromatic ketones in DMSO: Synthesis of 2-aryl or 2-hetarylindoles

Authors
Baumgartner, MT Nazareno, MA Murguia, MC Pierini, AB Rossi, RA
Citation
Mt. Baumgartner et al., Reaction of o-iodoaniline with aromatic ketones in DMSO: Synthesis of 2-aryl or 2-hetarylindoles, SYNTHESIS-S, (12), 1999, pp. 2053-2056
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
12
Year of publication
1999
Pages
2053 - 2056
Database
ISI
SICI code
0039-7881(199912):12<2053:ROOWAK>2.0.ZU;2-W
Abstract
The reactions of o-iodoaniline (1) with the enolate anions from acetone (2) , acetophenone (4), 2-acetylnaphthalene (6), 2-acetyl-1-methylpyrrole (8a) and 2-acetylthiophene (8b) in DMSO give respectively the corresponding 2-su bstituted indoles in 63, 88, 73, 93 and 82% yields. These reactions are pro posed to take place by an S(RN)1 mechanism. Depending on the ketone enolate ion involved, the reactions can occur under light or Fe(II) salts initiati on.