Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles

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 mixtu...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Monge, M.E., Bonesi, S.M., Erra-Balsells, R.
Formato: JOUR
Materias:
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
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_0022152X_v39_n5_p933_Monge
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

Ejemplares similares