Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism

SM Barolo, AE Lukach, RA Rossi

Index: Barolo, Silvia M.; Lukach, Andres E.; Rossi, Roberto A. Journal of Organic Chemistry, 2003 , vol. 68, # 7 p. 2807 - 2811

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Citation Number: 36

Abstract

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 ...