Syntheses of 2-Substituted Indoles and Fused Indoles by Photostimulated Reactions of o-Iodoanilines with Carbanions by the SRN1 Mechanism

SILVIA M. BAROLO; ANDRES E. LUKACH; ROBERTO A. ROSSI*

JOURNAL OF ORGANIC CHEMISTRY

Año: 2003 vol. 68 p. 2807 - 2807

0022-3263

p class="MsoNormal" style="MARGIN: 0cm 0cm 0pt; TEXT-ALIGN: justify; mso-layout-grid-align: none">2-Substituted indoles (5a,b and 7) and fused indoles (9a-c, 11a,b, and 12) have been obtained by the SRN1 mechanism from photostimulated reactions of o-iodoaniline (1) and 1-halo-2-naphthalen-2-ylamines (3a,b) with enolate ions of acyclic (acetophenone (6), 2- (4a) and 4-acetylpyridine (4b)) and cyclic ketones (1- (8a) and 2-indanone (10a), 1- (8b) and 2-tetralone (10b) and 1-benzosuberone (8c)) in DMSO and liquid ammonia as solvents. The carbanions derived from 4a,b, 8a, and 10b are novel nucleophiles that form new C