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Expedient Iodocyclization Approach Toward Polysubstituted 3 H ‐Benzo[ e ]indoles
Author(s) -
Martins Guilherme M.,
Zeni Gilson,
Back Davi F.,
Kaufman Teodoro S.,
Silveira Claudio C.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500275
Subject(s) - chemistry , nitromethane , dichloromethane , potassium carbonate , iodine , base (topology) , amine gas treating , medicinal chemistry , ethyl acetoacetate , chloride , organic chemistry , catalysis , solvent , mathematical analysis , mathematics
A facile and expedient iodocyclization of 4‐(2‐prop‐1‐ynylphenyl)‐1 H ‐pyrroles towards the synthesis of polysubstituted 3 H ‐benzo[ e ]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4‐tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride‐promoted four‐component (nitromethane, amine, 2‐alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5‐iodoheterocycles was also explored.