Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system
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-triiodo...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0022152X_v38_n1_p77_Bonesi |
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todo:paper_0022152X_v38_n1_p77_Bonesi2023-10-03T14:27:45Z Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system Bonesi, S.M. Erra-Balsells, R. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0022152X_v38_n1_p77_Bonesi |
| institution |
Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Bonesi, S.M. Erra-Balsells, R. Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Bonesi, S.M. Erra-Balsells, R. |
| author_facet |
Bonesi, S.M. Erra-Balsells, R. |
| author_sort |
Bonesi, S.M. |
| title |
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| title_short |
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| title_full |
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| title_fullStr |
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| title_full_unstemmed |
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system |
| title_sort |
synthesis and isolation of iodocarbazoles. direct iodination of carbazoles by n-iodosuccinimide and n-iodosuccinimide-silica gel system |
| url |
http://hdl.handle.net/20.500.12110/paper_0022152X_v38_n1_p77_Bonesi |
| work_keys_str_mv |
AT bonesism synthesisandisolationofiodocarbazolesdirectiodinationofcarbazolesbyniodosuccinimideandniodosuccinimidesilicagelsystem AT errabalsellsr synthesisandisolationofiodocarbazolesdirectiodinationofcarbazolesbyniodosuccinimideandniodosuccinimidesilicagelsystem |
| _version_ |
1807321786792017920 |