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

Autor:	and Andrés E. Lukach, Roberto A. Rossi, Silvia M. Barolo
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Ketone Radical-nucleophilic aromatic substitution Stereochemistry Organic Chemistry Medicinal chemistry Chemical synthesis chemistry.chemical_compound Ammonia chemistry Nucleophile Amine gas treating Acetophenone Carbanion
Zdroj:	The Journal of Organic Chemistry. 68:2807-2811
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo026672k
Popis:	2-Substituted indoles (5a,b and 7) and fused indoles (9a-c, 11a,b, and 12) have been obtained by the S(RN)1 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 S(RN)1 mechanism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::171cdc5423f651e8e5d997e214c65f51 https://doi.org/10.1021/jo026672k Zobrazit plný text záznamu