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Abstract:

Iododerivatives of N-methylcarbazole (1), N-phenylcarbazole (2), N-benzylcarbazole (3), 2-methoxy-N-methylcarbazole (4) and 3-acetamido-N-ethylcarbazole (5) are synthesised. N-Iodosuccinimide (NIS) in tetrahydrofurane/H2SO4 (catalyst), a mixture of KIO3 - KI - H2SO4 (catalyst) in ethanol and a mixture of KIO3 - KI in glacial AcOH as iodinating agents have been used and their uses have been compared. The preparation, isolation and characterization of compounds 1a, 1b, 1c, 1d, 2a, 2b, 3a, 3b, 4a, 4b, 4c and 5a are reported (mp, tR, Rf, 1H-nmr, 13C-nmr, IR and ms). All of them are described for the first time except 3,6-diiodo-N-phenylcarbazole (2b). Semiempirical PM3 calculations have been performed to predict reactivity of N-substituted carbazoles and their iododerivatives. Theoretical and experimental results are discussed briefly.

Registro:

Documento: Artículo
Título:Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
Autor:Monge, M.E.; Bonesi, S.M.; Erra-Balsells, R.
Filiación:Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1430-Buenos Aires, Argentina
Palabras clave:2 methoxy n methylcarbazole; 3 acetamido n ethylcarbazole; alcohol; carbazole derivative; carbon 13; iodocarbazole; n benzylcarbazole; n iodosuccinimide; n methylcarbazole; n phenylcarbazole; proton; succinimide derivative; sulfuric acid; tetrahydrofuran; unclassified drug; 3,6 iodo n phenylcarbazole; article; calculation; carbon nuclear magnetic resonance; catalyst; chemical parameters; chemical reaction; infrared radiation; iodination; isolation procedure; mass spectrometry; prediction; proton nuclear magnetic resonance; synthesis
Año:2002
Volumen:39
Número:5
Página de inicio:933
Página de fin:941
DOI: http://dx.doi.org/10.1002/jhet.5570390513
Título revista:Journal of Heterocyclic Chemistry
Título revista abreviado:J. Heterocycl. Chem.
ISSN:0022152X
CODEN:JHTCA
CAS:alcohol, 64-17-5; carbon 13, 14762-74-4; proton, 12408-02-5, 12586-59-3; sulfuric acid, 7664-93-9; tetrahydrofuran, 109-99-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v39_n5_p933_Monge

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Citas:

---------- APA ----------
Monge, M.E., Bonesi, S.M. & Erra-Balsells, R. (2002) . Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles. Journal of Heterocyclic Chemistry, 39(5), 933-941.
http://dx.doi.org/10.1002/jhet.5570390513
---------- CHICAGO ----------
Monge, M.E., Bonesi, S.M., Erra-Balsells, R. "Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles" . Journal of Heterocyclic Chemistry 39, no. 5 (2002) : 933-941.
http://dx.doi.org/10.1002/jhet.5570390513
---------- MLA ----------
Monge, M.E., Bonesi, S.M., Erra-Balsells, R. "Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles" . Journal of Heterocyclic Chemistry, vol. 39, no. 5, 2002, pp. 933-941.
http://dx.doi.org/10.1002/jhet.5570390513
---------- VANCOUVER ----------
Monge, M.E., Bonesi, S.M., Erra-Balsells, R. Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles. J. Heterocycl. Chem. 2002;39(5):933-941.
http://dx.doi.org/10.1002/jhet.5570390513