Producción CyT
Artículo
Autoría
MONGE, MARIA EUGENIA
;
Sergio M. Bonesi
;
Rosa Erra-Balsells
Fecha
2002
Editorial y Lugar de Edición
WILEY-BLACKWELL PUBLISHING, INC
Revista
JOURNAL OF HETEROCYCLIC CHEMISTRY,
vol. 39
(pp. 933-941)
WILEY-BLACKWELL PUBLISHING, INC
Resumen
Información suministrada por el agente en
SIGEVA
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,...
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.
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Palabras Clave
HALOGENATIONCARBAZOLE DERIVATIVES