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Abstract:

Carbazole (1) undergoes electrophilic aromatic substitution with various iodinating reagents. Although, 3-iodocarbazole (1b) and 3,6-diiodocarbazole (1d) obtained by iodination of carbazole were isolated and characterized sometime ago, 1-iodocarbazole (1a), 1,6-diiodocarbazole (1c) and 1,3,6-triiodocarbazole (1e) had never been isolated from the reaction mixture. The preparation and subsequent isolation and characterization of 1a, 1b, 1c, 1d and 1e are reported (mp, tr, Rf, 1H-nmr, 13C-nmr and ms). As iodinating reagents, NaIO4/I2 and NaIO4/KI mixtures in (i) ethanol doped with catalytical amount of sulfuric acid and in (ii) acetic acid, and N-iodosuccinimide and N-iodosuccinimide-silica gel in dichloromethane and in chloroform have been used and their uses have been compared. The iodination reaction of different carbazole derivatives such as 2-acetoxycarbazole (2), 3-bromocarbazole (3) and 3-nitrocarbazole (4) was also studied and the corresponding iododerivatives, 2a, 2b, 2c, 3a, 3b, 4a and 4b, are described for the first time. Semiempirical PM3 calculations have been performed in order to predict reactivity of carbazole (1), substituted carbazoles (2-4) and iodocarbazoles (1a-1e, 2a-2c, 3a-3b, 4a and 4b) (Scheme 1). Theoretical and experimental results are discussed briefly.

Registro:

Documento: Artículo
Título:Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system
Autor:Bonesi, S.M.; Erra-Balsells, R.
Filiación:Departamento de Quimica Organica, Facultad Ciencias Exactas Naturales, Universidad de Buenos Aires, cc. 74 - suc. 30, 1430-Buenos Aires, Argentina
Palabras clave:carbazole derivative; chloroform; dichloromethane; iodocarbazole derivative; silica gel; succinimide derivative; sulfuric acid; unclassified drug; article; calculation; carbon nuclear magnetic resonance; chemical analysis; chemical reaction; iodination; mass spectrometry; proton nuclear magnetic resonance; reaction analysis; synthesis
Año:2001
Volumen:38
Número:1
Página de inicio:77
Página de fin:87
DOI: http://dx.doi.org/10.1002/jhet.5570380111
Título revista:Journal of Heterocyclic Chemistry
Título revista abreviado:J. Heterocycl. Chem.
ISSN:0022152X
CODEN:JHTCA
CAS:chloroform, 67-66-3; dichloromethane, 75-09-2; silica gel, 63231-67-4; sulfuric acid, 7664-93-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v38_n1_p77_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M. & Erra-Balsells, R. (2001) . Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system. Journal of Heterocyclic Chemistry, 38(1), 77-87.
http://dx.doi.org/10.1002/jhet.5570380111
---------- CHICAGO ----------
Bonesi, S.M., Erra-Balsells, R. "Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system" . Journal of Heterocyclic Chemistry 38, no. 1 (2001) : 77-87.
http://dx.doi.org/10.1002/jhet.5570380111
---------- MLA ----------
Bonesi, S.M., Erra-Balsells, R. "Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system" . Journal of Heterocyclic Chemistry, vol. 38, no. 1, 2001, pp. 77-87.
http://dx.doi.org/10.1002/jhet.5570380111
---------- VANCOUVER ----------
Bonesi, S.M., Erra-Balsells, R. Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system. J. Heterocycl. Chem. 2001;38(1):77-87.
http://dx.doi.org/10.1002/jhet.5570380111