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...

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Autores principales:	Monge, María Eugenia, Bonesi, Sergio Mauricio, Erra Balsells, Rosa
Publicado:	2002
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:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v39_n5_p933_Monge 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

id	paper:paper_0022152X_v39_n5_p933_Monge
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spelling	paper:paper_0022152X_v39_n5_p933_Monge2023-06-08T14:46:49Z Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles Monge, María Eugenia Bonesi, Sergio Mauricio Erra Balsells, Rosa 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 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. Fil:Monge, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v39_n5_p933_Monge http://hdl.handle.net/20.500.12110/paper_0022152X_v39_n5_p933_Monge
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Monge, María Eugenia Bonesi, Sergio Mauricio Erra Balsells, Rosa Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
topic_facet	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
description	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.
author	Monge, María Eugenia Bonesi, Sergio Mauricio Erra Balsells, Rosa
author_facet	Monge, María Eugenia Bonesi, Sergio Mauricio Erra Balsells, Rosa
author_sort	Monge, María Eugenia
title	Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
title_short	Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
title_full	Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
title_fullStr	Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
title_full_unstemmed	Synthesis and isolation of iodocarbazoles. Direct iodination reaction 933 of N-substituted carbazoles
title_sort	synthesis and isolation of iodocarbazoles. direct iodination reaction 933 of n-substituted carbazoles
publishDate	2002
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v39_n5_p933_Monge http://hdl.handle.net/20.500.12110/paper_0022152X_v39_n5_p933_Monge
work_keys_str_mv	AT mongemariaeugenia synthesisandisolationofiodocarbazolesdirectiodinationreaction933ofnsubstitutedcarbazoles AT bonesisergiomauricio synthesisandisolationofiodocarbazolesdirectiodinationreaction933ofnsubstitutedcarbazoles AT errabalsellsrosa synthesisandisolationofiodocarbazolesdirectiodinationreaction933ofnsubstitutedcarbazoles
_version_	1768545220712988672

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

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