Reaction of o-Iodoaniline with Aromatic Ketones in DMSO. Synthesis of 2-Aryl or 2-Hetaryl Indoles.

BAUMGARTNER, M.T; NAZARENO, M.A.; MURGIA, M.C.; PIERINI, A. B.; ROSSI, R.A.

SYNTHESIS-STUTTGART

GEORG THIEME VERLAG KG

Año: 1999 p. 2053 - 2056

0039-7881

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 -substituted indoles in 63%, 88%, 73%, 93% and 82% yields. These reactions are proposed to take place by the SRN1 mechanism. Depending on the ketone enolate ion involved, the reactions can occur under light or Fe(II) salts initiation.