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Barolo SM, Lukach AE, Rossi RA. Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism. J Org Chem. 2003;68(7):2807-11doi: 10.1021/jo026672k.
Barolo, S. M., Lukach, A. E., & Rossi, R. A. (2003). Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism. The Journal of organic chemistry, 68(7), 2807-11. https://doi.org/10.1021/jo026672k
Barolo, Silvia M, et al. "Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism." The Journal of organic chemistry vol. 68,7 (2003): 2807-11. doi: https://doi.org/10.1021/jo026672k
Barolo SM, Lukach AE, Rossi RA. Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism. J Org Chem. 2003 Apr 04;68(7):2807-11. doi: 10.1021/jo026672k. PMID: 12662056.
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J Org Chem. 2003 Apr 04;68(7):2807-11. doi: 10.1021/jo026672k.

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

The Journal of organic chemistry

Silvia M Barolo, Andrés E Lukach, Roberto A Rossi

Affiliations

  1. INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.

PMID: 12662056 DOI: 10.1021/jo026672k

Abstract

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.

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