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Synthesis and isolation of iodocarbazoles. Direct iodination reaction of N ‐substituted carbazoles
Author(s) -
Monge María E.,
Bonesi Sergio M.,
ErraBalsells Rosa
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390513
Subject(s) - chemistry , carbazole , halogenation , reactivity (psychology) , catalysis , carbon 13 nmr , ethanol , organic chemistry , medicinal chemistry , medicine , alternative medicine , pathology
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.