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

✍ Scribed by María E. Monge; Sergio M. Bonesi; Rosa Erra-Balsells

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
57 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

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/H~2~SO~4~ (catalyst), a mixture of KIO~3~ ‐ KI ‐ H~2~SO~4~ (catalyst) in ethanol and a mixture of KIO~3~ ‐ 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, t~R~, R~f~, ^1^H‐nmr, ^13^C‐nmr, IR and ms). All of them are described for the first time except 3,6‐diiodo‐N‐phenyl‐carbazole (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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