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

Autor:	Roberto A. Rossi, Silvia M. Barolo, and Andrés E. Lukach
Rok vydání:	2003
Předmět:	chemistry.chemical_compound Radical-nucleophilic aromatic substitution Nucleophile Chemistry Liquid ammonia General Medicine Medicinal chemistry Acetophenone Ion Carbanion
Zdroj:	ChemInform. 34
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200332087
Popis:	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−C bonds by the SRN1 mechanism.
Databáze:	OpenAIRE
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